KR20110077205A - Novel 3-arylbutenolide derivatives and its preparation method - Google Patents

Novel 3-arylbutenolide derivatives and its preparation method Download PDF

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KR20110077205A
KR20110077205A KR1020090133701A KR20090133701A KR20110077205A KR 20110077205 A KR20110077205 A KR 20110077205A KR 1020090133701 A KR1020090133701 A KR 1020090133701A KR 20090133701 A KR20090133701 A KR 20090133701A KR 20110077205 A KR20110077205 A KR 20110077205A
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arylbutenolide
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이필호
이광무
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강원대학교산학협력단
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/58—One oxygen atom, e.g. butenolide
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/48—Silver or gold
    • B01J23/50—Silver
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/48—Silver or gold
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Abstract

PURPOSE: A 3-arylbutenolide derivative and a method for preparing the same are provided to develop a novel drug and various medicines. CONSTITUTION: A 3-arylbutenolide derivative is denoted by chemical formula 1. A method for preparing the 3-arylbutenolide derivative comprises a step of performing intramolecular cyclization of 2-aryl allenoate derivative of chemical formula 2 under the presence of gold(Au) catalyst and acid. The gold catalyst is monovalent AuBr, AuCl, or PPh_3AuCl, or trivalent AuBr_3 or AuCl_3. The acid is CF_3CO_2H, CH_3CO_2H, CF_3SO_3H.

Description

신규한 3-아릴부텐올라이드 유도체와 이의 제조방법{Novel 3-arylbutenolide derivatives and its preparation method}Novel 3-arylbutenolide derivatives and its preparation method

본 발명은 신규한 3-아릴부텐올라이드(3-arylbutenolide) 유도체와 이의 제조방법에 관한 것이다. 보다 상세하게는, 금(Au) 촉매와 소량의 산 존재 하에서 2-아릴알렌오에이트의 분자내 고리화 반응을 통해 상기 신규한 3-아릴부텐올라이드 유도체를 제조하는 방법에 관한 것이다.The present invention relates to novel 3-arylbutenolide derivatives and methods for their preparation. More particularly, the present invention relates to a process for preparing the novel 3-arylbutenolide derivatives via intramolecular cyclization of 2-arylalenate in the presence of a gold (Au) catalyst and a small amount of acid.

부텐올라이드 유도체는 천연물의 합성에 매우 중요한 중간체로 사용되며 특히 생물학적 활성을 가지는 부텐올라이드 유도체들은 펩타이드 유사체를 합성하기 위한 출발물질로 사용되며 의약품의 합성에도 이용된다. 따라서 이러한 부텐올라이드 유도체들의 합성법을 개발하기 위해 많은 연구가 보고되었다. 또한 부텐올라이드의 3번 또는 3번과 5번 위치에 치환기를 도입하기 위해 다양한 반응들이 소개되었다 (Tetrdhedron Lett . 1989, 30, 6109; Tetrdhedron Lett . 1992, 33, 7049; Synth. Commun . 1998, 28, 3305; Tetrdhedron Lett . 1999, 40, 989; Tetrdhedron Lett . 1999, 40, 1381; Bioorg . Med . Chem . Lett . 2000, 10, 1893; J. Comb. Chem . 2003, 5, 273; Bioorg . Med . Chem . 2003, 11, 2843; Synlett 2005, 538 ; Tetrdhedron Lett. 2007, 48, 1485; Chem . Commun . 2008, 6405).Buteneolide derivatives are used as intermediates which are very important for the synthesis of natural products. Especially, buteneolide derivatives with biological activity are used as starting materials for synthesizing peptide analogs and also for the synthesis of pharmaceuticals. Therefore, many studies have been reported to develop a method for synthesizing such buteneolide derivatives. In addition, various reactions have been introduced to introduce substituents at positions 3 or 3 and 5 of buteneolide ( Tetrdhedron Lett . 1989 , 30 , 6109; Tetrdhedron Lett . 1992 , 33 , 7049; Synth. Commun . 1998 , 28 , 3305; Tetrdhedron Lett . 1999 , 40 , 989; Tetrdhedron Lett . 1999 , 40 , 1381; Bioorg . Med . Chem . Lett . 2000 , 10 , 1893; J. Comb. Chem . 2003 , 5 , 273; Bioorg . Med . Chem . 2003 , 11 , 2843; Synlett 2005 , 538; Tetrdhedron Lett. 2007 , 48 , 1485; Chem . Commun . 2008 , 6405).

그러나, 상기 반응들은 부텐올라이드를 합성하기 위해 많은 실험과정을 거쳐야 하며 수율 또한 높은 편이 아니다. 더욱이 금 촉매를 이용한 2-아릴알렌오에이트의 분자내 고리화 반응을 통한 3-아릴부텐올라이드 유도체의 제조방법은 현재까지 문헌에 보고된 바 없다.However, the reactions require a lot of experiments to synthesize buteneolide, and the yield is not high. Furthermore, no method of preparing 3-arylbutenolide derivatives through intramolecular cyclization of 2-aryl alleneate using gold catalysts has been reported to date.

본 발명의 목적은 천연물의 합성에 매우 중요한 중간체로 작용할 뿐만 아니라 의약품의 합성에 이용되는 신규한 3-아릴부텐올라이드 유도체를 제공하는 데 있다. It is an object of the present invention to provide novel 3-arylbutenolide derivatives which serve as intermediates which are very important for the synthesis of natural products as well as for the synthesis of pharmaceuticals.

또한, 본 발명은 금 촉매와 소량의 산을 이용하여 2-아릴알렌오에이트 유도체의 분자내 고리화 반응을 통해 상기 신규한 3-아릴부텐올라이드 유도체를 제조하는 방법을 제공하는 데 또 다른 목적이 있다.Another object of the present invention is to provide a method for preparing the novel 3-arylbutenolide derivative by intramolecular cyclization of a 2-aryl alleneate derivative using a gold catalyst and a small amount of acid. There is this.

본 발명은 하기 화학식 1로 표시되는 3-아릴부텐올라이드(3-arylbutenolide) 유도체 및 이의 제조방법을 제공한다.The present invention provides a 3-arylbutenolide derivative represented by the following formula (1) and a preparation method thereof.

[화학식 1][Formula 1]

Figure 112009081503796-PAT00002
Figure 112009081503796-PAT00002

또한, 본 발명에 따른 상기 화학식 1의 3-아릴부텐올라이드 유도체의제조방법은 금(Au) 촉매 및 촉매량의 산 존재 하에 하기 화학식 2로 표시되는 2-아릴렌오에이트 유도체의 분자 내 고리화반응을 통하여 탄소-산소 결합을 유도함으로써 화학식 1의 3-아릴부텐올라이드 유도체를 제조하는 것을 특징으로 한다.In addition, the preparation method of the 3-arylbutenolide derivative of Chemical Formula 1 according to the present invention is an intramolecular cyclization reaction of the 2-aryleneoate derivative represented by Chemical Formula 2 in the presence of a gold (Au) catalyst and a catalytic amount of acid. By inducing a carbon-oxygen bond through is characterized in that the 3-arylbuteneolide derivative of formula (1) is prepared.

[화학식 2][Formula 2]

Figure 112009081503796-PAT00003
Figure 112009081503796-PAT00003

이하, 본 발명을 상세히 설명한다.Hereinafter, the present invention will be described in detail.

이때, 사용되는 기술 용어 및 과학 용어에 있어서 다른 정의가 없다면, 이 발명이 속하는 기술 분야에서 통상의 지식을 가진 자가 통상적으로 이해하고 있는 의미를 가진다. 또한, 종래와 동일한 기술적 구성 및 작용에 대한 반복되는 설명은 생략하기로 한다. At this time, if there is no other definition in the technical terms and scientific terms used, it has a meaning commonly understood by those of ordinary skill in the art. Repeated descriptions of the same technical constitution and operation as those of the conventional art will be omitted.

본 발명은 하기 화학식 1로 표시되는 3-아릴부텐올라이드(3-arylbutenolide) 유도체를 제공한다.The present invention provides a 3-arylbutenolide derivative represented by the following formula (1).

[화학식 1][Formula 1]

Figure 112009081503796-PAT00004
Figure 112009081503796-PAT00004

[상기 화학식 1에서 R1 및 R5는 서로 독립적으로 수소, (C1~C7)알킬, (C6~C20)아릴, 할로겐 또는 (C1~C7)알콕시카보닐이고; R2 및 R4는 서로 독립적으로 수소, (C1~C7)알콕시, 니트로 또는 할로겐이고; R3는 수소, (C1~C7)알킬, (C6~C20) 아릴, 할로겐, 포밀, 아세틸, (C1~C7)알콕시카보닐기 또는 (C6~C20)아릴(C1~C7)알킬카바모일(C6~C20)아릴이고; 상기 R1 내지 R5는 각각 독립적으로 서로 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 알킬렌 또는 알케닐렌으로 연결되어 융합고리를 형성할 수 있고; R6는 수소 또는 (C1~C7)알킬이다.][In Formula 1, R 1 and R 5 are each independently hydrogen, (C 1 -C 7) alkyl, (C 6 -C 20) aryl, halogen or (C 1 -C 7) alkoxycarbonyl; R 2 and R 4 independently of one another are hydrogen, (C 1 -C 7) alkoxy, nitro or halogen; R 3 is hydrogen, (C 1 -C 7) alkyl, (C 6 -C 20) aryl, halogen, formyl, acetyl, (C 1 -C 7) alkoxycarbonyl group or (C 6 -C 20) aryl (C 1 -C 7) alkylcarbamoyl (C 6 Aryl; Each of R 1 to R 5 may be independently connected to an alkylene or alkenylene including or without a substituent and a fused ring adjacent to each other to form a fused ring; R 6 is hydrogen or (C 1 -C 7 ) alkyl.]

상기 '알킬'은 직쇄상 또는 분쇄상의 탄소사슬을 모두 포함한다.The 'alkyl' includes both linear or pulverized carbon chains.

구체적으로 상기 화학식 1에서 R1 및 R5는 서로 독립적으로 수소, 메틸, 페닐, 클로로 또는 에톡시카보닐이고; R2 및 R4는 서로 독립적으로 수소, 메톡시, 니트로 또는 클로로이고; R3는 수소, 부틸, 페닐, 브로모, 클로로, 포밀, 아세틸, 에톡시카보닐, 페닐 또는 벤질카마모일페닐이고; 상기 R1 내지 R5는 각각 독립적으로 서로 인접한 치환체와

Figure 112009081503796-PAT00005
으로 연결되어 벤젠고리를 형성할 수 있고; R6는 수소, 메틸, 에틸 또는 프로필이다.Specifically, in Formula 1, R 1 and R 5 are each independently hydrogen, methyl, phenyl, chloro or ethoxycarbonyl; R 2 and R 4 are independently of each other hydrogen, methoxy, nitro or chloro; R 3 is hydrogen, butyl, phenyl, bromo, chloro, formyl, acetyl, ethoxycarbonyl, phenyl or benzylcamamoylphenyl; R 1 to R 5 are each independently a substituent adjacent to each other and
Figure 112009081503796-PAT00005
Connected to form a benzene ring; R 6 is hydrogen, methyl, ethyl or propyl.

본 발명의 3-아릴부텐올라이드 유도체는 하기 구조의 화합물로부터 선택되나, 이에 한정되는 것은 아니다.The 3-arylbutenolide derivative of the present invention is selected from, but is not limited to, a compound having the following structure.

Figure 112009081503796-PAT00006
Figure 112009081503796-PAT00006

또한, 본 발명은 상기 화학식 1로 표시되는 3-아릴부텐올라이드 유도체의 제조방법을 권리범위로 포함하는 바, 본 발명에 따른 3-아릴부텐올라이드 유도체의 제조방법에 대하여 상세히 설명한다.In addition, the present invention includes the preparation method of the 3-arylbutenolide derivative represented by Chemical Formula 1 as a right scope, and the method of preparing the 3-arylbutenolide derivative according to the present invention will be described in detail.

본 발명에 따른 3-아릴부텐올라이드 유도체의 제조방법은 금(Au) 촉매 및 촉매량의 산 존재 하에 하기 화학식 2로 표시되는 2-아릴알렌오에이트 유도체의 분자 내 고리화 반응을 통하여 하기 화학식 1의 3-아릴부텐올라이드 유도체를 제조하는 것을 특징으로 한다.Method for preparing a 3-arylbuteneolide derivative according to the present invention through the intramolecular cyclization reaction of the 2-aryl allene oate derivative represented by the following formula (2) in the presence of a gold (Au) catalyst and a catalytic amount of acid It is characterized by preparing a 3-arylbuteneolide derivative.

[화학식 1][Formula 1]

Figure 112009081503796-PAT00007
Figure 112009081503796-PAT00007

[화학식 2][Formula 2]

Figure 112009081503796-PAT00008
Figure 112009081503796-PAT00008

[상기 화학식 1 및 2에서 R1 및 R5는 서로 독립적으로 수소, (C1~C7)알킬, (C6~C20)아릴, 할로겐 또는 (C1~C7)알콕시카보닐이고; R2 및 R4는 서로 독립적으로 수소, (C1~C7)알콕시, 니트로 또는 할로겐이고; R3는 수소, (C1~C7)알킬, (C6~C20)아릴, 할로겐, 포밀, 아세틸, (C1~C7)알콕시카보닐기 또는 (C6~C20)아릴(C1~C7)알킬카바모일(C6~C20)아릴이고; 상기 R1 내지 R5는 각각 독립적으로 서로 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 알킬렌 또는 알케닐렌으로 연결되어 융합고리를 형성할 수 있고; R6는 수소 또는 (C1~C7)알킬이고; R은 (C1~C7)알킬 또는 (C6~C20)아릴이다.][In Formulas 1 and 2, R 1 and R 5 are each independently hydrogen, (C 1 -C 7) alkyl, (C 6 -C 20) aryl, halogen or (C 1 -C 7) alkoxycarbonyl; R 2 and R 4 independently of one another are hydrogen, (C 1 -C 7) alkoxy, nitro or halogen; R 3 is hydrogen, (C 1 -C 7) alkyl, (C 6 -C 20) aryl, halogen, formyl, acetyl, (C 1 -C 7) alkoxycarbonyl group or (C 6 -C 20) aryl (C 1 -C 7) alkylcarbamoyl (C 6 Aryl; Each of R 1 to R 5 may be independently connected to an alkylene or alkenylene including or without a substituent and a fused ring adjacent to each other to form a fused ring; R 6 is hydrogen or (C 1 -C 7 ) alkyl; R is (C1-C7) alkyl or (C6-C20) aryl.]

본 발명의 제조방법에서 사용되는 반응용기는 둥근바닥 플라스크 및 테스트 튜브(test tube)로 이루어진 군에서 선택되는 것이 바람직하며, 테스트 튜브(test tube)를 사용하는 것이 더욱 바람직하다. The reaction vessel used in the production method of the present invention is preferably selected from the group consisting of a round bottom flask and a test tube, more preferably using a test tube.

본 발명의 제조방법에서 사용되는 금(Au) 촉매는 1가 또는 3가의 할라이드계 금(Au)화합물을 사용하며, 1가의 금 촉매는 예를 들어 AuBr, AuCl, PPh3AuCl(Ph= phenyl) 등을 사용할 수 있고, 3가의 금 촉매는 AuBr3, AuCl3, 등을 사용할 수 있으며, AuCl3를 촉매로 사용하는 것이 보다 바람직하다.Gold (Au) catalyst used in the production method of the present invention uses a monovalent or trivalent halide-based gold (Au) compound, the monovalent gold catalyst is, for example, AuBr, AuCl, PPh 3 AuCl (Ph = phenyl) Etc. can be used, and as the trivalent gold catalyst, AuBr 3 , AuCl 3 , etc. can be used, and AuCl 3 is more preferably used as a catalyst.

본 발명의 제조방법에서 사용되는 금 촉매의 양은 상기 화학식 2로 표시되는 2-아릴알렌오에이트 유도체에 대해 1 내지 10 mol%를 사용하는 것이 바람직하며 5 mol%를 사용하는 것이 더욱 바람직하다.The amount of the gold catalyst used in the preparation method of the present invention is preferably used 1 to 10 mol% and more preferably 5 mol% based on the 2-aryl alloate derivative represented by the formula (2).

본 발명의 제조방법에서는 상기 금(Au) 촉매 외에 은(Ag) 촉매를 병용하여 금(Au) 촉매의 루이스 산도를 높임으로써 반응의 선택성 및 수율 측면에서 더욱 바람직하다. 상기 은(Ag) 촉매의 경우 AgOTf(OTf= trifluoromethane sulfonate), AgBF4, AgPF6, AgAsF6, AgNTf6, AgSbF6 및 AgNO3로 이루어진 군에서 선택되는 1종 이상이 바람직하며, AgOTf를 금 촉매와 병용 사용하는 것이 더욱 바람직하다.In the production method of the present invention, by using a silver (Ag) catalyst in addition to the gold (Au) catalyst to increase the Lewis acidity of the gold (Au) catalyst is more preferable in terms of selectivity and yield of the reaction. In the case of the silver (Ag) catalyst, one or more selected from the group consisting of AgOTf (OTf = trifluoromethane sulfonate), AgBF 4 , AgPF 6 , AgAsF 6 , AgNTf 6 , AgSbF 6, and AgNO 3 is preferable, and AgOTf is a gold catalyst. It is more preferable to use together with.

본 발명의 제조방법에서 사용되는 은(Ag) 촉매는 AuBr3, AuCl3와 같이 3가의 금(Au) 촉매를 사용하는 경우 은(Ag) 촉매는 금(Au) 촉매에 대해 2~4당량, 보다 좋게는 3당량을 사용한다. 또한 AuBr, AuCl, PPh3AuCl와 같이 1가의 금(Au) 촉매의 경우 은(Ag) 촉매는 금(Au) 촉매에 대해 0.5~1.5당량, 보다 좋게는 같은 촉매량을 사용하도록 하며, 은 촉매는 금 촉매에 대하여 통상 1 내지 30 mol%를 사용하는 것이 바람직하며 15 mol%를 사용하는 것이 더욱 바람직하다.The silver (Ag) catalyst used in the production method of the present invention is AuBr 3 , when using a trivalent gold (Au) catalyst such as AuCl 3 silver (Ag) catalyst is 2 to 4 equivalents to the gold (Au) catalyst, More preferably 3 equivalents. In the case of monovalent gold (Au) catalysts such as AuBr, AuCl, and PPh 3 AuCl, silver (Ag) catalysts should use 0.5 to 1.5 equivalents, and more preferably equal amounts of catalysts to gold (Au) catalysts. It is generally preferred to use 1 to 30 mol% and more preferably 15 mol% with respect to the gold catalyst.

본 발명의 제조방법에서 사용되는 산은 CF3CO2H, CH3CO2H 및CF3SO3H로 이루어지는 군으로부터 1종 이상 선택되는 것이 바람직하며 상기 화학식 2로 표시되는 2-아릴알렌오에이트 유도체의 4번 위치가 수소인 경우 CH3CO2H를 사용하는 것이 더욱 바람직하고, 상기 화학식 2로 표시되는 2-아릴알렌오에이트의 4번 위치가 알킬기를 가지는 경우 CF3SO3H를 사용하는 것이 더욱 바람직하다.The acid used in the preparation method of the present invention is preferably selected from one or more selected from the group consisting of CF 3 CO 2 H, CH 3 CO 2 H and CF 3 SO 3 H, 2-aryl allene oate represented by the formula (2) When position 4 of the derivative is hydrogen, it is more preferable to use CH 3 CO 2 H, and when position 4 of the 2-arylene alloate represented by Formula 2 has an alkyl group, CF 3 SO 3 H is used. More preferably.

본 발명의 제조방법에서 사용되는 산의 양은 상기 화학식 2로 표시되는2-아릴알렌오에이트 유도체에 대하여 1 내지 10 mol%을 사용하는 것이 바람직하며, 5 mol%을 사용하는 것이 더욱 바람직하다.The amount of acid used in the preparation method of the present invention is preferably used 1 to 10 mol%, more preferably 5 mol% based on the 2-aryl alloate derivative represented by the formula (2).

본 발명의 제조방법에서 사용되는 용매는 통상의 유기용매이며 다이클로로메탄(DCM), 다이클로로에탄(DCE), 톨루엔(Toluene), 아세토나이트릴(MeCN), 나이트로메탄(Nitromethane) 또는 이들의 혼합용매를 사용하는 것이 바람직하며, 다이클로로에탄(DCE)을 용매로 사용하는 것이 더욱 바람직하다.The solvent used in the preparation method of the present invention is a conventional organic solvent and dichloromethane (DCM), dichloroethane (DCE), toluene (Toluene), acetonitrile (MeCN), nitromethane or It is preferable to use a mixed solvent, more preferably using dichloroethane (DCE) as a solvent.

반응온도는 60 내지 100 ℃에서 상기 반응을 수행하며, 80 ℃에서 수행하는 것이 더욱 바람직하다. The reaction temperature is carried out at 60 to 100 ° C, more preferably at 80 ° C.

반응시간은 반응물질, 용매의 종류 및 용매의 양에 따라 달라질 수 있으며, TLC 등을 통하여 출발물질인 상기 화학식 2로 표시되는 2-아릴알렌오에이트 유도체가 완전히 소모됨을 확인한 후 반응을 완결시킨다. 반응이 완결되면 추출과정 후 감압 하에서 용매를 증류시킨 후 관 크로마토그래피 등의 통상의 방법을 통하여 목 적물을 분리 정제할 수 있다.The reaction time may vary depending on the reactants, the type of solvent, and the amount of the solvent. After confirming that the 2-aryl allene oate derivative represented by Chemical Formula 2 as a starting material is completely consumed through TLC, the reaction is completed. After completion of the reaction, the solvent may be distilled off under reduced pressure after the extraction process, and then the target may be separated and purified through a conventional method such as column chromatography.

본 발명에 따른 3-아릴부텐올라이드 유도체들은 천연물의 기본골격으로 사용될 뿐만 아니라 이를 통해 신약 개발 및 다양한 의약품의 개발이 가능하다. 또한 본 발명에 따른 금 촉매와 소량의 산을 이용한 2-아릴알렌오에이트 유도체의 분자내 고리화 반응을 통해 높은 수율과 간단한 실험과정으로 3-아릴부텐올라이드 유도체를 제조할 수 있는 장점을 가진다.The 3-arylbuteneolide derivatives according to the present invention can be used not only as a basic skeleton of natural products, but also for the development of new drugs and the development of various medicines. In addition, through the intramolecular cyclization reaction of the 2-aryl allene oate derivative using a gold catalyst and a small amount of the acid according to the present invention has the advantage of producing a 3-aryl butene olide derivative in a high yield and a simple experiment process .

이하, 실시예를 통하여 본 발명의 구성을 보다 구체적으로 설명하지만, 하기의 실시예들은 본 발명에 대한 이해를 돕기 위한 것으로서, 본 발명의 범위가 여기에 국한된 것은 아니다.Hereinafter, the configuration of the present invention in more detail through examples, the following examples are provided to help the understanding of the present invention, the scope of the present invention is not limited thereto.

[실시예 1] 3-페닐퓨란-2-(5H)-온 (3-phenylfuran-2-(5H)-one)의 제조Preparation of one (3-phenylfuran-2- (5 H) -one) - [ Example 1] 3-phenyl-furan -2- (5 H)

Figure 112009081503796-PAT00009
Figure 112009081503796-PAT00009

질소분위기 하에서 테스트 튜브에 AuCl3 (7.6 mg, 0.025 mmol), AgOTf (19.2 mg, 0.075 mmol)을 넣고 다이클로로에탄 (1 mL)를 넣어 실온에서 5 분간 교반시킨 후 여기에 에틸 2-페닐-2,3-부타다이엔오에이트 (94 mg, 0.5 mmol)와 아세트산 (0.8 mg, 0.025 mmol)을 각각 다이클로로에탄 (0.5 mL)에 녹여 첨가하였다. 이 혼합물을 80℃에서 2 시간 교반시킨 후 반응을 종결시켰다. 실온으로 온도를 낮춘 뒤 다이클로로메탄 (20 mL x 3)으로 추출하고 물 (20 mL)과 포화 NaCl 수용액 (20 mL)으로 씻어주었다. 추출한 유기층은 무수 MgSO4로 건조하고 여과하였다. 용매를 제거한 후 관 크로마토그래피로 분리하여, 표제화합물인 3-페닐퓨란-2-(5H)-온 (60 mg, 75%)를 얻었다.Under a nitrogen atmosphere, AuCl 3 (7.6 mg, 0.025 mmol) and AgOTf (19.2 mg, 0.075 mmol) were added to a test tube, dichloroethane (1 mL) was added thereto, stirred at room temperature for 5 minutes, and then ethyl 2-phenyl-2 was added thereto. , 3-Butadienoate (94 mg, 0.5 mmol) and acetic acid (0.8 mg, 0.025 mmol) were each dissolved in dichloroethane (0.5 mL) and added. The mixture was stirred at 80 ° C. for 2 hours before the reaction was terminated. After cooling to room temperature, the mixture was extracted with dichloromethane (20 mL x 3) and washed with water (20 mL) and saturated aqueous NaCl solution (20 mL). The extracted organic layer was dried over anhydrous MgSO 4 and filtered. The solvent was removed and the residue was separated by column chromatography to obtain 3-phenylfuran-2- ( 5H ) -one (60 mg, 75%) as a title compound.

1H NMR (400 MHz, CDCl3) δ 7.85 (d, J = 4.02 Hz, 2H), 7.65 (t, J = 1.95 Hz, 1H), 7.45-7.37 (m, 3H), 4.92 (d, J = 4.02 Hz, 3H) 1 H NMR (400 MHz, CDCl 3 ) δ 7.85 (d, J = 4.02 Hz, 2H), 7.65 (t, J = 1.95 Hz, 1H), 7.45-7.37 (m, 3H), 4.92 (d, J = 4.02 Hz, 3H)

[실시예 2] 3-(3-메톡시페닐)퓨란-2(5H)-온 (3-(3-methoxyphenyl) furan-2(5H)-one)의 제조Example 2 3- (3-methoxyphenyl) furan -2 (5 H) - Preparation of a whole (3- (3-methoxyphenyl) furan -2 (5 H) -one)

Figure 112009081503796-PAT00010
Figure 112009081503796-PAT00010

질소분위기 하에서 테스트 튜브에 AuCl3 (7.6 mg, 0.025 mmol), AgOTf (19.2 mg, 0.075 mmol)을 넣고 다이클로로에탄 (1 mL)를 넣어 실온에서 5 분간 교반시킨 후 여기에 에틸 2-(3-메톡시페닐)-2,3-부타다이엔오에이트 (109 mg, 0.5 mmol)와 아세트산 (0.8 mg, 0.025 mmol)을 각각 다이클로로에탄 (0.5 mL)에 녹여 첨가하였다. 이 혼합물을 80℃에서 3 시간 교반시킨 후 반응을 종결시켰다. 실온으로 온도 를 낮춘 뒤 다이클로로메탄 (20 mL x 3)으로 추출하고 물 (20 mL)과 포화 NaCl 수용액 (20 mL)으로 씻어주었다. 추출한 유기층은 무수 MgSO4로 건조하고 여과하였다. 용매를 제거한 후 관 크로마토그래피로 분리하여, 표제화합물인 3-(3-메톡시페닐)퓨란-2(5H)-온 (67 mg, 70%)를 얻었다.In a nitrogen atmosphere, AuCl 3 (7.6 mg, 0.025 mmol) and AgOTf (19.2 mg, 0.075 mmol) were added to a test tube, dichloroethane (1 mL) was added thereto, stirred at room temperature for 5 minutes, and then ethyl 2- (3- Methoxyphenyl) -2,3-butadienoate (109 mg, 0.5 mmol) and acetic acid (0.8 mg, 0.025 mmol) were each dissolved in dichloroethane (0.5 mL) and added. The mixture was stirred at 80 ° C. for 3 hours before the reaction was terminated. After cooling to room temperature, the mixture was extracted with dichloromethane (20 mL x 3) and washed with water (20 mL) and saturated aqueous NaCl solution (20 mL). The extracted organic layer was dried over anhydrous MgSO 4 and filtered. The solvent was removed and the residue was separated by column chromatography to obtain the title compound 3- (3-methoxyphenyl) furan-2 ( 5H ) -one (67 mg, 70%).

1H NMR (400 MHz, CDCl3) δ 7.65 (s, 1H), 7.45 (d, J = 1.97, 1H), 7.41 (d, J = 7.71, 1H), 7.33 (t, J = 7.93 Hz, 1H), 6.94 (d, J = 8.15, 1H), 4.92 (d, J = 1.97 Hz, 2H), 3.84 (s, 3H) 1 H NMR (400 MHz, CDCl 3 ) δ 7.65 (s, 1H), 7.45 (d, J = 1.97, 1H), 7.41 (d, J = 7.71, 1H), 7.33 (t, J = 7.93 Hz, 1H ), 6.94 (d, J = 8.15, 1H), 4.92 (d, J = 1.97 Hz, 2H), 3.84 (s, 3H)

[실시예 3] 3-(4-브로모페닐)퓨란-2(5H)-온 (3-(4-bromophenyl) furan-2(5H)-one)의 제조Preparation of one (3- (4-bromophenyl) furan -2 (5 H) -one) - [ Example 3] 3- (4-bromophenyl) furan -2 (5 H)

Figure 112009081503796-PAT00011
Figure 112009081503796-PAT00011

질소분위기 하에서 테스트 튜브에 AuCl3 (7.6 mg, 0.025 mmol), AgOTf (19.2 mg, 0.075 mmol)을 넣고 다이클로로에탄 (1 mL)를 넣어 실온에서 5 분간 교반시킨 후 여기에 에틸 2-(4-브로모페닐)-2,3-부타다이엔오에이트 (133 mg, 0.5 mmol)와 아세트산 (0.8 mg, 0.025 mmol)을 각각 다이클로로에탄 (0.5 mL)에 녹여 첨가하였다. 이 혼합물을 80℃에서 2 시간 교반시킨 후 반응을 종결시켰다. 실온으로 온도를 낮춘 뒤 다이클로로메탄 (20 mL x 3)으로 추출하고 물 (20 mL)과 포화 NaCl 수 용액 (20 mL)으로 씻어주었다. 추출한 유기층은 무수 MgSO4로 건조하고 여과하였다. 용매를 제거한 후 관 크로마토그래피로 분리하여, 표제화합물인 3-(4-브로모페닐)퓨란-2(5H)-온 (92 mg, 77%)를 얻었다.In a nitrogen atmosphere, AuCl 3 (7.6 mg, 0.025 mmol) and AgOTf (19.2 mg, 0.075 mmol) were added to a test tube, dichloroethane (1 mL) was added thereto, stirred at room temperature for 5 minutes, and then ethyl 2- (4- Bromophenyl) -2,3-butadienoate (133 mg, 0.5 mmol) and acetic acid (0.8 mg, 0.025 mmol) were each dissolved in dichloroethane (0.5 mL) and added. The mixture was stirred at 80 ° C. for 2 hours before the reaction was terminated. After cooling to room temperature, the mixture was extracted with dichloromethane (20 mL x 3) and washed with water (20 mL) and saturated NaCl aqueous solution (20 mL). The extracted organic layer was dried over anhydrous MgSO 4 and filtered. The solvent was removed and the residue was separated by column chromatography to obtain 3- (4-bromophenyl) furan-2 ( 5H ) -one (92 mg, 77%) as a title compound.

1H NMR (400 MHz, CDCl3) δ 7.76 (d, J = 8.61 Hz, 2H), 7.67 (d, J = 2.0 Hz, 1H), 7.56 (d, J = 8.80 Hz, 2H), 4.93 (d, J = 2.0 Hz, 2H) 1 H NMR (400 MHz, CDCl 3 ) δ 7.76 (d, J = 8.61 Hz, 2H), 7.67 (d, J = 2.0 Hz, 1H), 7.56 (d, J = 8.80 Hz, 2H), 4.93 (d, J = 2.0 Hz, 2H)

[실시예 4] 5-메틸-3-페닐퓨란-2(5H)-온 (5-methyl-3-phenylfuran-2(5H)-one)의 제조Preparation of one (5-methyl-3-phenylfuran -2 (5 H) -one) - [ Example 4] 5-Methyl-3-phenyl-furan -2 (5 H)

Figure 112009081503796-PAT00012
Figure 112009081503796-PAT00012

질소분위기 하에서 테스트 튜브에 AuCl3 (7.6 mg, 0.025 mmol), AgOTf (19.2 mg, 0.075 mmol)을 넣고 다이클로로에탄 (1 mL)를 넣어 실온에서 5 분간 교반시킨 후 여기에 에틸 2-페닐-2,3-펜타다이엔오에이트 (101 mg, 0.5 mmol)와 트리플루오로메탄설폰산 (1.9 mg, 0.025 mmol)을 각각 다이클로로에탄 (0.5 mL)에 녹여 첨가하였다. 이 혼합물을 80℃에서 1 시간 교반시킨 후 반응을 종결시켰다. 실온으로 온도를 낮춘 뒤 다이클로로메탄 (20 mL x 3)으로 추출하고 물 (20 mL)과 포화 NaCl 수용액 (20 mL)으로 씻어주었다. 추출한 유기층은 무수 MgSO4로 건조하고 여과하였다. 용매를 제거한 후 관 크로마토그래피로 분리하여, 표제화합물인 5-메틸-3-페닐 퓨란-2(5H)-온 (74 mg, 85%)를 얻었다.Under a nitrogen atmosphere, AuCl 3 (7.6 mg, 0.025 mmol) and AgOTf (19.2 mg, 0.075 mmol) were added to a test tube, dichloroethane (1 mL) was added thereto, stirred at room temperature for 5 minutes, and then ethyl 2-phenyl-2 was added thereto. , 3-pentadienoate (101 mg, 0.5 mmol) and trifluoromethanesulfonic acid (1.9 mg, 0.025 mmol) were each dissolved in dichloroethane (0.5 mL) and added. The mixture was stirred at 80 ° C. for 1 hour before the reaction was terminated. After cooling to room temperature, the mixture was extracted with dichloromethane (20 mL x 3) and washed with water (20 mL) and saturated aqueous NaCl solution (20 mL). The extracted organic layer was dried over anhydrous MgSO 4 and filtered. The solvent was removed and the residue was separated by column chromatography to obtain 5-methyl-3-phenylfuran-2 ( 5H ) -one (74 mg, 85%) as a title compound.

1H NMR (400 MHz, CDCl3) δ 7.87-7.84 (m, 2H), 7.55 (d, J = 1.80 Hz, 1H), 7.42-7.38 (m, 3H), 5.16 (td, J = 6.83, 1.80 Hz, 1H), 1.52 (d, J = 6.83 Hz, 3H) 1 H NMR (400 MHz, CDCl 3 ) δ 7.87-7.84 (m, 2H), 7.55 (d, J = 1.80 Hz, 1H), 7.42-7.38 (m, 3H), 5.16 (td, J = 6.83, 1.80 Hz, 1H), 1.52 (d, J = 6.83 Hz, 3H)

[실시예 5] 5-메틸-3-(2-메틸페닐)퓨란-2(5H)-온 (5-methyl-3-(2-methylphenyl)furan-2-5(H)-one)의 제조Example 5 5-methyl-3- (2-methylphenyl) furan -2 (5 H) - Preparation of on (5-methyl-3- (2 -methylphenyl) furan-2-5 (H) -one)

Figure 112009081503796-PAT00013
Figure 112009081503796-PAT00013

질소분위기 하에서 테스트 튜브에 AuCl3 (7.6 mg, 0.025 mmol), AgOTf (19.2 mg, 0.075 mmol)을 넣고 다이클로로에탄 (1 mL)를 넣어 실온에서 5 분간 교반시킨 후 여기에 에틸 2-(2-메틸페닐)-2,3-펜타다이엔오에이트 (108 mg, 0.5 mmol)와 트리플루오로메탄설폰산 (1.9 mg, 0.025 mmol)을 각각 다이클로로에탄 (0.5 mL)에 녹여 첨가하였다. 이 혼합물을 80℃에서 3 시간 교반시킨 후 반응을 종결시켰다. 실온으로 온도를 낮춘 뒤 다이클로로메탄 (20 mL x 3)으로 추출하고 물 (20 mL)과 포화 NaCl 수용액 (20 mL)으로 씻어주었다. 추출한 유기층은 무수 MgSO4로 건조하고 여과하였다. 용매를 제거한 후 관 크로마토그래피로 분리하여, 표제화합물인 5-메틸-3-(2-메틸페닐)퓨란-2(5H)-온 (72 mg, 77%)를 얻었다.Under a nitrogen atmosphere, AuCl 3 (7.6 mg, 0.025 mmol) and AgOTf (19.2 mg, 0.075 mmol) were added to the test tube, dichloroethane (1 mL) was added thereto, and stirred at room temperature for 5 minutes, followed by ethyl 2- (2- Methylphenyl) -2,3-pentadienoate (108 mg, 0.5 mmol) and trifluoromethanesulfonic acid (1.9 mg, 0.025 mmol) were each dissolved in dichloroethane (0.5 mL) and added. The mixture was stirred at 80 ° C. for 3 hours before the reaction was terminated. After cooling to room temperature, the mixture was extracted with dichloromethane (20 mL x 3) and washed with water (20 mL) and saturated aqueous NaCl solution (20 mL). The extracted organic layer was dried over anhydrous MgSO 4 and filtered. After removal of the solvent and separated by column chromatography to give the title compound 5-methyl-3- (2-methylphenyl) furan -2 (5 H) - one was obtained (72 mg, 77%).

1H NMR (400 MHz, CDCl3) δ 7.61 (d, J = 7.32 Hz, 1H), 7.48 (d, J = 1.82 Hz, 1H), 7.32-7.21 (m, 3H), 4.91 (d, J = 1.82 Hz), 2.41 (s, 3H), 1.51 (d, J = 6.81 Hz, 3H) 1 H NMR (400 MHz, CDCl 3 ) δ 7.61 (d, J = 7.32 Hz, 1H), 7.48 (d, J = 1.82 Hz, 1H), 7.32-7.21 (m, 3H), 4.91 (d, J = 1.82 Hz), 2.41 (s, 3H), 1.51 (d, J = 6.81 Hz, 3H)

[실시예 6] 메틸 3-(2-클로로페닐)-5-메틸퓨란-2(5H)-온 (3-(2-chloro-phenyl)-5-methylfuran-2(5H)-one)의 제조Example 6 Methyl 3- (2-Chloro-phenyl) -5-methyl-furan -2 (5 H) - one (3- (2-chloro-phenyl ) -5-methylfuran-2 (5 H) -one) Manufacture

Figure 112009081503796-PAT00014
Figure 112009081503796-PAT00014

질소분위기 하에서 테스트 튜브에 AuCl3 (7.6 mg, 0.025 mmol), AgOTf (19.2 mg, 0.075 mmol)을 넣고 다이클로로에탄 (1 mL)를 넣어 실온에서 5 분간 교반시킨 후 여기에 에틸 2-(2-클로로페닐)-2,3-펜타다이엔오에이트 (118 mg, 0.5 mmol)와 트리플루오로메탄설폰산 (1.9 mg, 0.025 mmol)을 각각 다이클로로에탄 (0.5 mL)에 녹여 첨가하였다. 이 혼합물을 80℃에서 4 시간 교반시킨 후 반응을 종결시켰다. 실온으로 온도를 낮춘 뒤 다이클로로메탄 (20 mL x 3)으로 추출하고 물 (20 mL)과 포화 NaCl 수용액 (20 mL)으로 씻어주었다. 추출한 유기층은 무수 MgSO4로 건조하고 여과하였다. 용매를 제거한 후 관 크로마토그래피로 분리하여, 표제화합물인 3-(2-클로로페닐)-5-메틸퓨란-2(5H)-온 (75 mg, 72%)를 얻었다.Under a nitrogen atmosphere, AuCl 3 (7.6 mg, 0.025 mmol) and AgOTf (19.2 mg, 0.075 mmol) were added to the test tube, dichloroethane (1 mL) was added thereto, and stirred at room temperature for 5 minutes, followed by ethyl 2- (2- Chlorophenyl) -2,3-pentadienoate (118 mg, 0.5 mmol) and trifluoromethanesulfonic acid (1.9 mg, 0.025 mmol) were each dissolved in dichloroethane (0.5 mL) and added. The mixture was stirred at 80 ° C. for 4 hours before the reaction was terminated. After cooling to room temperature, the mixture was extracted with dichloromethane (20 mL x 3) and washed with water (20 mL) and saturated aqueous NaCl solution (20 mL). The extracted organic layer was dried over anhydrous MgSO 4 and filtered. The solvent was removed and the residue was separated by column chromatography to obtain the title compound 3- (2-chlorophenyl) -5-methylfuran-2 ( 5H ) -one (75 mg, 72%).

1H NMR (400 MHz, CDCl3) δ 7.72 (d, J = 1.90 Hz, 1H), 7.70-7.65 (m, 1H), 7.50-7.45 (m, 1H), 7.36-7.30 (m, 2H), 5.24-5.21 (m, 1H), 1.55 (d, J = 6.92 Hz, 3H) 1 H NMR (400 MHz, CDCl 3 ) δ 7.72 (d, J = 1.90 Hz, 1H), 7.70-7.65 (m, 1H), 7.50-7.45 (m, 1H), 7.36-7.30 (m, 2H), 5.24-5.21 (m, 1H), 1.55 (d, J = 6.92 Hz, 3H)

[실시예 7] 3-(4-브로모페닐)-5-메틸퓨란-2(5H)-온 (3-(4-bromo-phenyl)-5-methylfuran-2(5H)-one)의 제조Example 7 3- (4-bromophenyl) -5-methyl-furan -2 (5 H) - one (3- (4-bromo-phenyl ) -5-methylfuran-2 (5 H) -one) Manufacture

Figure 112009081503796-PAT00015
Figure 112009081503796-PAT00015

질소분위기 하에서 테스트 튜브에 AuCl3 (7.6 mg, 0.025 mmol), AgOTf (19.2 mg, 0.075 mmol)을 넣고 다이클로로에탄 (1 mL)를 넣어 실온에서 5 분간 교반시킨 후 여기에 에틸 2-(4-브로모페닐)-2,3-펜타다이엔오에이트 (140 mg, 0.5 mmol)와 트리플루오로메탄설폰산 (1.9 mg, 0.025 mmol)을 각각 다이클로로에탄 (0.5 mL)에 녹여 첨가하였다. 이 혼합물을 80℃에서 4 시간 교반시킨 후 반응을 종결시켰다. 실온으로 온도를 낮춘 뒤 다이클로로메탄 (20 mL x 3)으로 추출하고 물 (20 mL)과 포화 NaCl 수용액 (20 mL)으로 씻어주었다. 추출한 유기층은 무수 MgSO4로 건조하고 여과하였다. 용매를 제거한 후 관 크로마토그래피로 분리하여, 표제화합물인 3-(4-브로모페닐)-5-메틸퓨란-2(5H)-온 (99 mg, 78%)를 얻었다.In a nitrogen atmosphere, AuCl 3 (7.6 mg, 0.025 mmol) and AgOTf (19.2 mg, 0.075 mmol) were added to a test tube, dichloroethane (1 mL) was added thereto, stirred at room temperature for 5 minutes, and then ethyl 2- (4- Bromophenyl) -2,3-pentadienoate (140 mg, 0.5 mmol) and trifluoromethanesulfonic acid (1.9 mg, 0.025 mmol) were each dissolved in dichloroethane (0.5 mL) and added. The mixture was stirred at 80 ° C. for 4 hours before the reaction was terminated. After cooling to room temperature, the mixture was extracted with dichloromethane (20 mL x 3) and washed with water (20 mL) and saturated aqueous NaCl solution (20 mL). The extracted organic layer was dried over anhydrous MgSO 4 and filtered. The solvent was removed and the residue was separated by column chromatography to obtain 3- (4-bromophenyl) -5-methylfuran-2 ( 5H ) -one (99 mg, 78%) as a title compound.

1H NMR (400 MHz, CDCl3) δ 7.76 (d, J = 8.61 Hz, 2H), 7.67 (d, J = 2.0 Hz, 1H), 7.55 (d, J = 8.80 Hz, 2H), 4.92 (d, d, J = 2.0 Hz, 2H), 1.50 (d, J = 6.84 Hz, 3H) 1 H NMR (400 MHz, CDCl 3 ) δ 7.76 (d, J = 8.61 Hz, 2H), 7.67 (d, J = 2.0 Hz, 1H), 7.55 (d, J = 8.80 Hz, 2H), 4.92 (d , d, J = 2.0 Hz, 2H), 1.50 (d, J = 6.84 Hz, 3H)

[실시예 8] 3-(3,4-다이클로로페닐)-5-메틸퓨란-2(5H)-온 (3-(3,4-dichlorophenyl)-5-methylfuran-2(5H)-one)의 제조Example 8 3- (3,4-dichloro-phenyl) -5-methyl-furan -2 (5 H) - one (3- (3,4-dichlorophenyl) -5 -methylfuran-2 (5 H) - manufacture of one)

Figure 112009081503796-PAT00016
Figure 112009081503796-PAT00016

질소분위기 하에서 테스트 튜브에 AuCl3 (7.6 mg, 0.025 mmol), AgOTf (19.2 mg, 0.075 mmol)을 넣고 다이클로로에탄 (1 mL)를 넣어 실온에서 5 분간 교반시킨 후 여기에 에틸 2-(3,4-다이클로로페닐)-2,3-펜타다이엔오에이트 (136 mg, 0.5 mmol)와 트리플루오로메탄설폰산 (1.9 mg, 0.025 mmol)을 각각 다이클로로에탄 (0.5 mL)에 녹여 첨가하였다. 이 혼합물을 80℃에서 4 시간 교반시킨 후 반응을 종결시켰다. 실온으로 온도를 낮춘 뒤 다이클로로메탄 (20 mL x 3)으로 추출하고 물 (20 mL)과 포화 NaCl 수용액 (20 mL)으로 씻어주었다. 추출한 유기층은 무수 MgSO4로 건조하고 여과하였다. 용매를 제거한 후 관 크로마토그래피로 분리하여, 표제화합물인 3-(3,4-다이클로로페닐)-5-메틸퓨란-2(5H)-온 (85 mg, 70%)를 얻었다.In a nitrogen atmosphere, AuCl 3 (7.6 mg, 0.025 mmol) and AgOTf (19.2 mg, 0.075 mmol) were added to a test tube, dichloroethane (1 mL) was added thereto, stirred at room temperature for 5 minutes, and then ethyl 2- (3, 4-dichlorophenyl) -2,3-pentadienoate (136 mg, 0.5 mmol) and trifluoromethanesulfonic acid (1.9 mg, 0.025 mmol) were each dissolved in dichloroethane (0.5 mL) and added. . The mixture was stirred at 80 ° C. for 4 hours before the reaction was terminated. After cooling to room temperature, the mixture was extracted with dichloromethane (20 mL x 3) and washed with water (20 mL) and saturated aqueous NaCl solution (20 mL). The extracted organic layer was dried over anhydrous MgSO 4 and filtered. The solvent was removed and the residue was separated by column chromatography to obtain 3- (3,4-dichlorophenyl) -5-methylfuran-2 ( 5H ) -one (85 mg, 70%) as a title compound.

1H NMR (400 MHz, CDCl3) δ 7.98 (d, J = 1.90 Hz, 1H), 7.74 (dd, J = 8.41, 1.90 Hz, 1H) 7.60 (d, J = 1.90 Hz, 1H), 7.48 (d, J = 1.40 Hz, 1H), 5.19-5.16 (m, 1H), 1.54 (d, J = 6.93 Hz, 3H) 1 H NMR (400 MHz, CDCl 3 ) δ 7.98 (d, J = 1.90 Hz, 1H), 7.74 (dd, J = 8.41, 1.90 Hz, 1H) 7.60 (d, J = 1.90 Hz, 1H), 7.48 ( d, J = 1.40 Hz, 1H), 5.19-5.16 (m, 1H), 1.54 (d, J = 6.93 Hz, 3H)

[실시예 9] 3-(4-에톡시카보닐페닐)-5-메틸퓨란-2(5H)-온 (3-(4-ethoxycarbonylphenyl)-5-methylfuran-2(5H)-one)의 제조Example 9 3- (4-ethoxycarbonyl-phenyl) -5-methyl-furan -2 (5 H) - one (3- (4-ethoxycarbonylphenyl) -5 -methylfuran-2 (5 H) -one) Manufacture

Figure 112009081503796-PAT00017
Figure 112009081503796-PAT00017

질소분위기 하에서 테스트 튜브에 AuCl3 (7.6 mg, 0.025 mmol), AgOTf (19.2 mg, 0.075 mmol)을 넣고 다이클로로에탄 (1 mL)를 넣어 실온에서 5 분간 교반시킨 후 여기에 에틸 2-(4-에톡시카보닐페닐)-2,3-펜타다이엔오에이트 (137 mg, 0.5 mmol)와 트리플루오로메탄설폰산 (1.9 mg, 0.025 mmol)을 각각 다이클로로에탄 (0.5 mL)에 녹여 첨가하였다. 이 혼합물을 80℃에서 2 시간 교반시킨 후 반응을 종결시켰다. 실온으로 온도를 낮춘 뒤 다이클로로메탄 (20 mL x 3)으로 추출하고 물 (20 mL)과 포화 NaCl 수용액 (20 mL)으로 씻어주었다. 추출한 유기층은 무수 MgSO4로 건조하고 여과하였다. 용매를 제거한 후 관 크로마토그래피로 분리하여, 표제화합물인 3-(4-에톡시카보닐페닐)-5-메틸퓨란-2(5H)-온 (89 mg, 72%)를 얻었다.In a nitrogen atmosphere, AuCl 3 (7.6 mg, 0.025 mmol) and AgOTf (19.2 mg, 0.075 mmol) were added to a test tube, dichloroethane (1 mL) was added thereto, stirred at room temperature for 5 minutes, and then ethyl 2- (4- Ethoxycarbonylphenyl) -2,3-pentadienoate (137 mg, 0.5 mmol) and trifluoromethanesulfonic acid (1.9 mg, 0.025 mmol) were added in dichloroethane (0.5 mL), respectively. . The mixture was stirred at 80 ° C. for 2 hours before the reaction was terminated. After cooling to room temperature, the mixture was extracted with dichloromethane (20 mL x 3) and washed with water (20 mL) and saturated aqueous NaCl solution (20 mL). The extracted organic layer was dried over anhydrous MgSO 4 and filtered. The solvent was removed and the residue was separated by column chromatography to obtain 3- (4-ethoxycarbonylphenyl) -5-methylfuran-2 ( 5H ) -one (89 mg, 72%) as a title compound.

1H NMR (400 MHz, CDCl3) δ 8.08 (d, J = 6.68 Hz, 2H), 7.94 (d, J = 6.68 Hz, 2H), 7.68 (d, J = 1.79 Hz, 1H), 5.19 (td, J = 6.89, 1.79 Hz, 1H), 4.40 (q, J = 7.12 Hz, 3H), 1.54 (d, J = 6.89 Hz, 3H), 1.41 (t, J = 7.12 Hz, 3H) 1 H NMR (400 MHz, CDCl 3 ) δ 8.08 (d, J = 6.68 Hz, 2H), 7.94 (d, J = 6.68 Hz, 2H), 7.68 (d, J = 1.79 Hz, 1H), 5.19 (td , J = 6.89, 1.79 Hz, 1H), 4.40 (q, J = 7.12 Hz, 3H), 1.54 (d, J = 6.89 Hz, 3H), 1.41 (t, J = 7.12 Hz, 3H)

[실시예 10] 5-에틸-3-(4-메틸페닐)퓨란-2(5H)-온 (5-ethyl-3-(4-methylphenyl)furan-2(5H)-one)의 제조Preparation of on (5-ethyl-3- (4 -methylphenyl) furan-2 (5 H) -one) - [ Example 10] 5-ethyl-3- (4-methylphenyl) furan -2 (5 H)

Figure 112009081503796-PAT00018
Figure 112009081503796-PAT00018

질소분위기 하에서 테스트 튜브에 AuCl3 (7.6 mg, 0.025 mmol), AgOTf (19.2 mg, 0.075 mmol)을 넣고 다이클로로에탄 (1 mL)를 넣어 실온에서 5 분간 교반시킨 후 여기에 에틸 2-(4-메틸페닐)-2,3-헥사다이엔오에이트 (115 mg, 0.5 mmol)와 트리플루오로메탄설폰산 (1.9 mg, 0.025 mmol)을 각각 다이클로로에탄 (0.5 mL)에 녹여 첨가하였다. 이 혼합물을 80℃에서 3 시간 교반시킨 후 반응을 종결시켰다. 실온으로 온도를 낮춘 뒤 다이클로로메탄 (20 mL x 3)으로 추출하고 물 (20 mL)과 포화 NaCl 수용액 (20 mL)으로 씻어주었다. 추출한 유기층은 무수 MgSO4로 건조하고 여과하였다. 용매를 제거한 후 관 크로마토그래피로 분리하여, 표제화합물인 5-에틸-3-(4-메틸페닐)퓨란-2(5H)-온 (79 mg, 78%)를 얻었다.In a nitrogen atmosphere, AuCl 3 (7.6 mg, 0.025 mmol) and AgOTf (19.2 mg, 0.075 mmol) were added to a test tube, dichloroethane (1 mL) was added thereto, stirred at room temperature for 5 minutes, and then ethyl 2- (4- Methylphenyl) -2,3-hexadienoate (115 mg, 0.5 mmol) and trifluoromethanesulfonic acid (1.9 mg, 0.025 mmol) were added dissolved in dichloroethane (0.5 mL), respectively. The mixture was stirred at 80 ° C. for 3 hours before the reaction was terminated. After cooling to room temperature, the mixture was extracted with dichloromethane (20 mL x 3) and washed with water (20 mL) and saturated aqueous NaCl solution (20 mL). The extracted organic layer was dried over anhydrous MgSO 4 and filtered. After removal of the solvent tube separated by chromatography to give the title compound 5-ethyl-3- (4-methylphenyl) furan -2 (5 H) - one was obtained (79 mg, 78%).

1H NMR (400 MHz, CDCl3) δ 7.70-7.73 (m, 2H), 7.49 (d, J = 1.9 Hz, 1H), 7.26-7.19 (m, 2H), 5.02-4.96 (m, 1H), 2.37 (s, 3H), 1.97-1.69 (m, 2H), 1.07 (t, J = 7.42 Hz, 3H) 1 H NMR (400 MHz, CDCl 3 ) δ 7.70-7.73 (m, 2H), 7.49 (d, J = 1.9 Hz, 1H), 7.26-7.19 (m, 2H), 5.02-4.96 (m, 1H), 2.37 (s, 3H), 1.97-1.69 (m, 2H), 1.07 (t, J = 7.42 Hz, 3H)

[실시예 11] 3-페닐-5-프로필퓨란-2(5H)-온 (3-phenyl-5-propyl-furan-2(5H)-one)의 제조Preparation of one (3-phenyl-5-propyl -furan-2 (5 H) -one) - [ Example 11] 3-phenyl-5-propyl-furan -2 (5 H)

Figure 112009081503796-PAT00019
Figure 112009081503796-PAT00019

질소분위기 하에서 테스트 튜브에 AuCl3 (7.6 mg, 0.025 mmol), AgOTf (19.2 mg, 0.075 mmol)을 넣고 다이클로로에탄 (1 mL)를 넣어 실온에서 5 분간 교반시킨 후 여기에 에틸 2-페닐-2,3-헵타다이엔오에이트 (115 mg, 0.5 mmol)와 트리플루오로메탄설폰산 (1.9 mg, 0.025 mmol)을 각각 다이클로로에탄 (0.5 mL)에 녹여 첨가하였다. 이 혼합물을 80℃에서 3 시간 교반시킨 후 반응을 종결시켰다. 실온으로 온도를 낮춘 뒤 다이클로로메탄 (20 mL x 3)으로 추출하고 물 (20 mL)과 포화 NaCl 수용액 (20 mL)으로 씻어주었다. 추출한 유기층은 무수 MgSO4로 건조하고 여과하였다. 용매를 제거한 후 관 크로마토그래피로 분리하여, 표제화합물인 3-페닐-5-프로필퓨란-2(5H)-온 (60 mg, 59%)를 얻었다.Under a nitrogen atmosphere, AuCl 3 (7.6 mg, 0.025 mmol) and AgOTf (19.2 mg, 0.075 mmol) were added to a test tube, dichloroethane (1 mL) was added thereto, stirred at room temperature for 5 minutes, and then ethyl 2-phenyl-2 was added thereto. , 3-heptadieoate (115 mg, 0.5 mmol) and trifluoromethanesulfonic acid (1.9 mg, 0.025 mmol) were each dissolved in dichloroethane (0.5 mL) and added. The mixture was stirred at 80 ° C. for 3 hours before the reaction was terminated. After cooling to room temperature, the mixture was extracted with dichloromethane (20 mL x 3) and washed with water (20 mL) and saturated aqueous NaCl solution (20 mL). The extracted organic layer was dried over anhydrous MgSO 4 and filtered. The solvent was removed and the residue was separated by column chromatography to obtain 3-phenyl-5-propylfuran-2 ( 5H ) -one (60 mg, 59%) as a title compound.

1H NMR (400 MHz, CDCl3) δ 7.86-7.84 (m, 2H), 7.55 (d, J = 1.78 Hz, 1H), 7.41-7.38 (m, 3H), 5.07-5.03 (m, 1H), 1.80-1.71 (m, 2H), 1.58-1.52 (m, 2H), 1.00 (t, J = 7.33 Hz, 3H) 1 H NMR (400 MHz, CDCl 3 ) δ 7.86-7.84 (m, 2H), 7.55 (d, J = 1.78 Hz, 1H), 7.41-7.38 (m, 3H), 5.07-5.03 (m, 1H), 1.80-1.71 (m, 2H), 1.58-1.52 (m, 2H), 1.00 (t, J = 7.33 Hz, 3H)

[실시예 12] 3-(3-메톡시페닐)-5-프로필퓨란-2(5H)-온 (3-(3-methoxyphenyl)-5-propylfuran-2(5H)-one)의 제조Preparation of one (3- (3-methoxyphenyl) -5 -propylfuran-2 (5 H) -one) - [ Example 12] 3- (3-methoxyphenyl) furan-5-propyl -2 (5 H)

Figure 112009081503796-PAT00020
Figure 112009081503796-PAT00020

질소분위기 하에서 테스트 튜브에 AuCl3 (7.6 mg, 0.025 mmol), AgOTf (19.2 mg, 0.075 mmol)을 넣고 다이클로로에탄 (1 mL)를 넣어 실온에서 5 분간 교반시킨 후 여기에 에틸 2-(3-메톡시페닐)-2,3-헵타다이엔오에이트 (130 mg, 0.5 mmol)와 트리플루오로메탄설폰산 (1.9 mg, 0.025 mmol)을 각각 다이클로로에탄 (0.5 mL)에 녹여 첨가하였다. 이 혼합물을 80℃에서 5 시간 교반시킨 후 반응을 종결시켰다. 실온으로 온도를 낮춘 뒤 다이클로로메탄 (20 mL x 3)으로 추출하고 물 (20 mL)과 포화 NaCl 수용액 (20 mL)으로 씻어주었다. 추출한 유기층은 무수 MgSO4로 건조하고 여과하였다. 용매를 제거한 후 관 크로마토그래피로 분리하여, 표제화합물인 3-(3-메톡시페닐)-5-프로필퓨란-2(5H)-온 (87 mg, 75%)를 얻었다.In a nitrogen atmosphere, AuCl 3 (7.6 mg, 0.025 mmol) and AgOTf (19.2 mg, 0.075 mmol) were added to a test tube, dichloroethane (1 mL) was added thereto, stirred at room temperature for 5 minutes, and then ethyl 2- (3- Methoxyphenyl) -2,3-heptadieoate (130 mg, 0.5 mmol) and trifluoromethanesulfonic acid (1.9 mg, 0.025 mmol) were each dissolved in dichloroethane (0.5 mL) and added. The mixture was stirred at 80 ° C. for 5 hours before the reaction was terminated. After cooling to room temperature, the mixture was extracted with dichloromethane (20 mL x 3) and washed with water (20 mL) and saturated aqueous NaCl solution (20 mL). The extracted organic layer was dried over anhydrous MgSO 4 and filtered. The solvent was removed and the residue was separated by column chromatography to obtain 3- (3-methoxyphenyl) -5-propylfuran-2 ( 5H ) -one (87 mg, 75%) as a title compound.

1H NMR (400 MHz, CDCl3) δ 7.64 (s, 1H), 7.42 (d, J = 1.97, 1H), 7.40 (d, J = 7.71, 1H), 7.33 (t, J = 7.93 Hz, 1H), 6.94 (d, J = 8.15, 1H), 4.90 (d, J = 1.97 Hz, 2H), 3.82 (s, 3H), 1.76-1.70 (m, 2H), 1.54-1.48 (m, 2H), 1.00 (t, J = 7.31 Hz, 3H) 1 H NMR (400 MHz, CDCl 3 ) δ 7.64 (s, 1H), 7.42 (d, J = 1.97, 1H), 7.40 (d, J = 7.71, 1H), 7.33 (t, J = 7.93 Hz, 1H ), 6.94 (d, J = 8.15, 1H), 4.90 (d, J = 1.97 Hz, 2H), 3.82 (s, 3H), 1.76-1.70 (m, 2H), 1.54-1.48 (m, 2H), 1.00 (t, J = 7.31 Hz, 3H)

Claims (12)

하기 화학식 1로 표시되는 3-아릴부텐올라이드(3-arylbutenolide) 유도체:3-arylbutenolide derivatives represented by Formula 1 below: [화학식 1][Formula 1]
Figure 112009081503796-PAT00021
Figure 112009081503796-PAT00021
 [상기 화학식 1에서 R1 및 R5는 서로 독립적으로 수소, (C1~C7)알킬, (C6~C20)아릴, 할로겐 또는 (C1~C7)알콕시카보닐이고; R2 및 R4는 서로 독립적으로 수소, (C1~C7)알콕시, 니트로 또는 할로겐이고; R3는 수소, (C1~C7)알킬, (C6~C20)아릴, 할로겐, 포밀, 아세틸, (C1~C7)알콕시카보닐기 또는 (C6~C20)아릴(C1~C7)알킬카바모일(C6~C20)아릴이고; 상기 R1 내지 R5는 각각 독립적으로 서로 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 알킬렌 또는 알케닐렌으로 연결되어 융합고리를 형성할 수 있고; R6는 수소 또는 (C1~C7)알킬이다.][In Formula 1, R 1 and R 5 are each independently hydrogen, (C 1 -C 7) alkyl, (C 6 -C 20) aryl, halogen or (C 1 -C 7) alkoxycarbonyl; R 2 and R 4 independently of one another are hydrogen, (C 1 -C 7) alkoxy, nitro or halogen; R 3 is hydrogen, (C 1 -C 7) alkyl, (C 6 -C 20) aryl, halogen, formyl, acetyl, (C 1 -C 7) alkoxycarbonyl group or (C 6 -C 20) aryl (C 1 -C 7) alkylcarbamoyl (C 6 Aryl; Each of R 1 to R 5 may be independently connected to an alkylene or alkenylene including or without a substituent and a fused ring adjacent to each other to form a fused ring; R 6 is hydrogen or (C 1 -C 7 ) alkyl.] 제 1항에 있어서, The method of claim 1, 상기 R1 및 R5는 서로 독립적으로 수소, 메틸, 페닐, 클로로 또는 에톡시카보닐이고; R2 및 R4는 서로 독립적으로 수소, 메톡시, 니트로 또는 클로로이고; R3 는 수소, 부틸, 페닐, 브로모, 클로로, 포밀, 아세틸, 에톡시카보닐, 페닐 또는 벤질카마모일페닐이고; 상기 R1 내지 R5는 각각 독립적으로 서로 인접한 치환체와
Figure 112009081503796-PAT00022
으로 연결되어 벤젠고리를 형성할 수 있고; R6는 수소, 메틸, 에틸 또는 프로필인 것을 특징으로 하는 3-아릴부텐올라이드 유도체.R 1 and R 5 are independently of each other hydrogen, methyl, phenyl, chloro or ethoxycarbonyl; R 2 and R 4 are independently of each other hydrogen, methoxy, nitro or chloro; R 3 is hydrogen, butyl, phenyl, bromo, chloro, formyl, acetyl, ethoxycarbonyl, phenyl or benzylcamamoylphenyl; R 1 to R 5 are each independently a substituent adjacent to each other and
Figure 112009081503796-PAT00022
Connected to form a benzene ring; R 6 is hydrogen, methyl, ethyl or propyl, 3-arylbutenolide derivative. 제 2항에 있어서,3. The method of claim 2, 상기 3-아릴부텐올라이드 유도체는 하기 구조의 화합물로부터 선택되는 것을 특징으로 하는 3-아릴부텐올라이드 유도체:3-arylbutenolide derivatives, characterized in that selected from compounds of the following structure:
Figure 112009081503796-PAT00023
Figure 112009081503796-PAT00023
 금(Au) 촉매 및 촉매량의 산 존재 하에 하기 화학식 2로 표시되는 2-아릴 알렌오에이트 유도체의 분자 내 고리화 반응을 통하여 하기 화학식 1의 3-아릴부텐올라이드 유도체를 제조하는 것을 특징으로 하는 3-아릴부텐올라이드 유도체의 제조방법.In the presence of a gold (Au) catalyst and a catalytic amount of acid, the 3-arylbuteneolide derivative of Formula 1 is prepared by intramolecular cyclization of a 2-aryl alloate derivative represented by Formula 2 below. Process for the preparation of 3-arylbutenolide derivatives. [화학식 1][Formula 1]
Figure 112009081503796-PAT00024
Figure 112009081503796-PAT00024
 [화학식 2][Formula 2]
Figure 112009081503796-PAT00025
Figure 112009081503796-PAT00025
 [상기 화학식 1 및 2에서 R1 및 R5는 서로 독립적으로 수소, (C1~C7)알킬, (C6~C20)아릴, 할로겐 또는 (C1~C7)알콕시카보닐이고; R2 및 R4는 서로 독립적으로 수소, (C1~C7)알콕시, 니트로 또는 할로겐이고; R3는 수소, (C1~C7)알킬, (C6~C20)아릴, 할로겐, 포밀, 아세틸, (C1~C7)알콕시카보닐기 또는 (C6~C20)아릴(C1~C7)알킬카바모일(C6~C20)아릴이고; 상기 R1 내지 R5는 각각 독립적으로 서로 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 알킬렌 또는 알케닐렌으로 연결되어 융 합고리를 형성할 수 있고; R6는 수소 또는 (C1~C7)알킬이고; R은 (C1~C7)알킬 또는 (C6~C20)아릴이다.][In Formulas 1 and 2, R 1 and R 5 are each independently hydrogen, (C 1 -C 7) alkyl, (C 6 -C 20) aryl, halogen or (C 1 -C 7) alkoxycarbonyl; R 2 and R 4 independently of one another are hydrogen, (C 1 -C 7) alkoxy, nitro or halogen; R 3 is hydrogen, (C 1 -C 7) alkyl, (C 6 -C 20) aryl, halogen, formyl, acetyl, (C 1 -C 7) alkoxycarbonyl group or (C 6 -C 20) aryl (C 1 -C 7) alkylcarbamoyl (C 6 Aryl; Each of R 1 to R 5 may be independently connected to an alkylene or alkenylene including or without a substituent and a fused ring adjacent to each other to form a fused ring; R 6 is hydrogen or (C 1 -C 7 ) alkyl; R is (C1-C7) alkyl or (C6-C20) aryl.] 제 4항에 있어서,The method of claim 4, wherein 상기 금(Au) 촉매는 1가의 금 촉매로서 AuBr, AuCl 또는 PPh3AuCl로부터 선택되거나, 3가의 금촉매로서 AuBr3, 또는 AuCl3로부터 선택되는 것을 특징으로 하는 3-아릴부텐올라이드 유도체의 제조방법.The gold (Au) catalyst is selected from AuBr, AuCl or PPh 3 AuCl as a monovalent gold catalyst, or AuBr 3 or AuCl 3 as a trivalent gold catalyst. Way. 제 5항에 있어서, The method of claim 5, 상기 금(Au) 촉매 외에 AgOTf, AgBF4, AgPF6, AgAsF6, AgNTf2, AgSbF6 및 AgNO3로 이루어진 군에서 선택되는 은(Ag) 촉매를 병용하는 것을 특징으로 하는 3-아릴부텐올라이드 유도체의 제조방법.AgOTf, AgBF 4 , AgPF 6 , AgAsF 6 , AgNTf 2 , AgSbF 6 in addition to the gold (Au) catalyst And a silver (Ag) catalyst selected from the group consisting of AgNO 3 . 제 6 항에 있어서, The method of claim 6, 상기 은 촉매의 사용량은 3가의 금(Au) 촉매를 사용하는 경우 금(Au) 촉매에 대해 2 내지 4 당량이고, 1가의 금(Au) 촉매를 사용하는 경우 0.5 내지 1.5당량인 것을 특징으로 하는 3-아릴부텐올라이드 유도체의 제조방법.The amount of the silver catalyst used is 2 to 4 equivalents to the gold (Au) catalyst when using a trivalent gold (Au) catalyst, 0.5 to 1.5 equivalents when using a monovalent gold (Au) catalyst Process for the preparation of 3-arylbutenolide derivatives. 제 5항에 있어서,The method of claim 5, 상기 금 촉매는 2-아릴 알렌오에이트 유도체에 대하여 1 내지 10mol%로 사용하는 것을 특징으로 하는 3-아릴부텐올라이드 유도체의 제조방법.The gold catalyst is a method for producing a 3-arylbutenolide derivative, characterized in that used in 1 to 10mol% relative to the 2-aryl alloate derivative. 제 5항에 있어서,The method of claim 5, 상기 산은 CF3CO2H, CH3CO2H 및 CF3SO3H로 이루어지는 군으로부터 1종 이상인 것을 특징으로 하는 3-아릴부텐올라이드 유도체의 제조방법.The acid is a method for producing a 3-arylbutenolide derivative, characterized in that at least one member from the group consisting of CF 3 CO 2 H, CH 3 CO 2 H and CF 3 SO 3 H. 제 9항에 있어서,The method of claim 9, 상기 산은 2-아릴 알렌오에이트 유도체에 대하여 1 내지 10 mol%를 사용하는 것을 특징으로 하는 3-아릴부텐올라이드 유도체의 제조방법.The acid is a method for producing a 3-arylbutenolide derivative, characterized in that 1 to 10 mol% based on 2-aryl alloate derivative. 제 4항에 있어서,The method of claim 4, wherein 상기 고리화반응은 다이클로로메탄(dichloromethane), 다이클로로에탄(dichloroethane), 톨루엔(toluene), 아세토나이트릴(acetonitrile), 나이트로메탄(Nitromethane) 및 이들의 혼합용매로부터 선택되는 용매 하에서 수행하는 것을 특징으로 하는 3-아릴부텐올라이드 유도체의 제조방법.The cyclization reaction is carried out in a solvent selected from dichloromethane, dichloroethane, toluene, toluene, acetonitrile, nitromethane and a mixed solvent thereof. Method for producing a 3-arylbuteneolide derivative characterized in that. 제 5항에 있어서,The method of claim 5, 상기 반응은 60 내지 100℃에서 다이클로로에탄(dichloroethane)을 용매로 하여 수행되는 것을 특징으로 하는 제조방법.The reaction is carried out at 60 to 100 ℃ using a dichloroethane (dichloroethane) as a solvent.
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