KR20120056585A - Synthesis method of stemofuran or derivatives thereof - Google Patents

Synthesis method of stemofuran or derivatives thereof Download PDF

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KR20120056585A
KR20120056585A KR1020100118198A KR20100118198A KR20120056585A KR 20120056585 A KR20120056585 A KR 20120056585A KR 1020100118198 A KR1020100118198 A KR 1020100118198A KR 20100118198 A KR20100118198 A KR 20100118198A KR 20120056585 A KR20120056585 A KR 20120056585A
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stemofuran
benzofuran
synthesize
dimethoxyphenyl
formula
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이용록
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영남대학교 산학협력단
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
    • A61K31/343—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide condensed with a carbocyclic ring, e.g. coumaran, bufuralol, befunolol, clobenfurol, amiodarone
    • 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
    • B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
    • B01J23/44—Palladium
    • 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
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C07D307/80—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

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  • Chemical Kinetics & Catalysis (AREA)
  • Furan Compounds (AREA)

Abstract

PURPOSE: A method for synthesizing stemofuran or derivative thereof is provided to ensure various physiological activity and to simply synthesize stemofuran A, stemofuran C, and derivative thereof. CONSTITUTION: A method for synthesizing stemofuran or derivative thereof comprises: a step of Suzuki coupling of 2-benzofuran boronic acid and 3,5-dimethoxy bromobenzene under the presence of Pd(PPh3)4 to synthesize 2-(3,5-dimethoxyphenyl)benzofuran; and a step of demethylating the methyl group of 2-(3,5-dimethoxyphenyl)benzofuran.

Description

Synthesis method of stemofuran or derivatives

The present invention relates to a novel synthesis method capable of simply synthesizing stemofuran or derivatives thereof having various physiological activities using a Suzuki coupling reaction.

Ste parent furan A-F is separated from the Stemona collinsae, S.tuberose S.peirrei and mainly distributed in East Asia, these plants is a medicinal plant that has been traditionally used in Asia for the treatment of inflammatory diseases. In addition, these plants have been used as anti-asthma medicine in Vietnamese folk.

In addition, compounds isolated from these plants are known to have leukotriene formation inhibitory activity, as well as antifungal and antibacterial activity. Therefore, a new synthetic method of these compounds having such important physiological activity is in progress.

Currently known stemofuran A synthesis is known to be synthesized from 2-hydroxybenzaldehyde through hydroxy group protection and deprotection related conversion ( Chem . Abstr . 2003, 139 , 36375). Another method is known to be synthesized from phenylboronic acid in four steps including [3,3] -sigma bond relocation as an important step ( Eur. J. Org. Chem . 2007, 1491).

However, there is still a need for a simple and efficient synthesis method capable of synthesizing stemofuran A to F having various physiological activities, and in particular, there is no report on the entire synthesis method of stemofuran C.

Accordingly, the present inventors have conducted various researches to efficiently and simply synthesize a stemofuran compound, and thus have various physiological activities using 2- (3,5-dimethoxyphenyl) benzofuran synthesized through Suzuki coupling reaction. The present invention was completed by discovering that stemofuran or a derivative thereof can be synthesized simply.

It is an object of the present invention to provide a novel synthesis method capable of efficiently and simply synthesizing stemofuran A, stemofuran C or derivatives thereof.

In order to achieve the above object, the present invention is synthesized by performing the Suzuki coupling reaction between 2-benzofuran boronic acid and 3,5-dimethoxybromobenzene in the presence of Pd (PPh 3 ) 4 2- (3,5- It provides a method for synthesizing stemofuran or a derivative thereof, using dimethoxyphenyl) benzofuran.

According to one embodiment of the present invention, the method for synthesizing stemofuran or derivatives thereof is performed by a Suzuki coupling reaction between 2-benzofuran boronic acid and 3,5-dimethoxybromobenzene in the presence of Pd (PPh 3 ) 4. Synthesizing 2- (3,5-dimethoxyphenyl) benzofuran; And demethylating the methyl group of 2- (3,5-dimethoxyphenyl) benzofuran to synthesize stemofuran A of Formula 1 below, and the detailed process is the same as in Scheme 1:

[Formula 1]

Figure pat00001

According to another embodiment of the present invention, the method for synthesizing stemofuran or derivatives thereof performs a Suzuki coupling reaction between 2-benzofuran boronic acid and 3,5-dimethoxybromobenzene in the presence of Pd (PPh 3 ) 4. To synthesize 2- (3,5-dimethoxyphenyl) benzofuran; Adding n-BuLi to the 2- (3,5-dimethoxyphenyl) benzofuran, and then adding methyl iodide to synthesize 2- (3,5-dimethoxy-4-methylphenyl) benzofuran ; And demethylating a part of the methyl group of 2- (3,5-dimethoxy-4-methylphenyl) benzofuran to synthesize stemofuran C of Formula 3 below, and a more detailed process is represented by Scheme 1 Is the same as:

(3)

Figure pat00002

Scheme 1

Figure pat00003

Further, according to another embodiment of the present invention, further comprising the step of reacting the stemofuran A reflux with α, β-unsaturated aldehyde in the presence of ethylenediamine diacetate to synthesize a stemofuran derivative of the formula (2) can do:

[Formula 2]

Figure pat00004

In Formula 2, R 1 is selected from hydrogen or a methyl group, R 2 may be selected from a methyl group, benzyl group or prenyl group.

The α, β-unsaturated aldehyde can be used any one selected from the group consisting of 3-methyl-2-butenal, trans-cinnamaldehyde and citral, in particular benzene or xyl to increase the yield of the stemofuran compound Preference is given to carrying out the reflux reaction under the lene solvent.

According to the synthesis method of the present invention, it is possible to easily synthesize stemofuran A, stemofuran C, and derivatives thereof which occur naturally and exhibit various physiological activities.

Hereinafter, the present invention will be described in more detail with reference to the following examples. However, the present invention is not limited by these examples.

All experiments below were performed under a nitrogen atmosphere. To measure analytical TLC, pre-coated silica gel plates (Art. 5554) with a Merck fluorescent indicator were used. Flash column chromatography was performed using silica gel 9385 (Merck). And 1 H NMR and 13 C NMR analyzes were recorded via Bruker Model ARX (300 and 75 MHz) spectroscopy in CDCl 3, CD 3 OD or acetone- d 6 as solvent chemical shifts. IR analysis was measured using a Jasco FTIR 5300 spectrometer. HRMS and MS analysis were performed by Korea Basic Science Institute.

Example 1 Synthesis of 2- (3,5-dimethoxyphenyl) benzofuran (11)

THF / H 2 O (1: 1) (30 mL) in 2-benzofuranboronic acid (0.486 g, 3.0 mmol), 3,5-dimethoxybromobenzene (0.651g, 3.0 mmol) and K 2 CO 3 (0.806 g, 4.2 mmol) was dissolved in a mixture of Pd (PPh 3 ) 4 (0.175 g, 0.15 mmol) under a nitrogen atmosphere, and the reaction mixture was heated under reflux for 8 hours. The reaction mixture was quenched with saturated NH 4 Cl solution (30 mL) and extracted with ethyl acetate (3 × 30 mL). The resulting extract was washed with water (30 mL), dried over MgSO 4 , and the solvent was evaporated under reduced pressure. Flash chromatography on silica gel using hexanes / ethyl acetate (5: 1) gave oily compound 11 (0.503 g, 66%).

1 H NMR (300 MHz, CDCl 3 ) δ 7.68-7.61 (2H, m), 7.42-7.30 (2H, m), 7.12 (2H, s), 7.09 (1H, s), 6.57 (1H, br s) , 3.95 (6H, s);

13 C NMR (75 MHz, CDCl 3 ) δ 161.1, 155.7, 154.8, 132.2, 129.1, 124.3, 122.9, 120.9, 111.1, 103.0, 101.8, 101.0, 55.4;

IR (neat): 3063, 2952, 1605, 1459, 1354, 1250, 1202, 1158, 1067, 944, 843, 747 cm −1 ;

HRMS m / z (M + ) calcd for C 16 H 14 O 3 : 254.0943. Found: 254.0945.

Example 2 Synthesis of Stemofuran A (1)

Reaction obtained by adding compound 11 (0.51 g, 2.0 mmol) prepared above at 0 ° C. to a solution of boron tribromide (2.4 mL, 1.0 M in CH 2 Cl 2 , 2.4 mmol) in methylene chloride (30 mL). The mixture was stirred at 0 ° C for 5 h. Ice water (30 mL) was added to the reaction mixture, which was then extracted with methylene chloride (3 × 30 mL), washed with water and dried over anhydrous sodium sulfate. After solvent removal, flash chromatography on silica gel using hexanes / ethyl acetate (3: 1) gave compound 1 (0.412 g, 91%) as a solid.

mp 181-182 ° C;

1 H NMR (300 MHz, CD 3 OD) δ 7.46 (1H, d, J = 8.0 Hz), 7.38 (1H, d, J = 8.0 Hz), 7.18-7.06 (2H, m), 6.93 (1H, d , J = 1.5 Hz), 6.74 (2H, dd, J = 1.5,1.5 Hz), 6.20 (1H, s), 4.78 (2H, brs);

13 C NMR (75 MHz, CD 3 OD) δ 160.0, 157.4, 156.1, 133.4, 130.5, 125.3, 124.0, 121.9, 111.8, 104.5, 104.1, 102.3;

IR (KBr) 3331, 1620, 1579, 1449, 1358, 1246, 1148, 999, 953, 853, 833, 801, 748 cm −1 ;

EIMS m / z (%) 226 (M + , 100), 197 (11), 181 (2), 169 (3), 152 (4), 151 (3), 150 (4), 141 (4), 139 (3), 115 (5), 113 (5);

HRMS m / z (M + ) calcd for C 14 H 10 O 3 : 226.0630. Found: 226.0631.

Example 3 Synthesis of 2- (3,5-dimethoxy-4-methylphenyl) benzofuran (12)

To the solution of Compound 1 (0.181 g, 0.8 mmol) in THF (20 mL) was added n- BuLi (0.36 mL, 2.5 M in hexane, 0.9 mmol) at 0 ° C. for 2 hours at 0 ° C. Stirred. Methyl iodide (0.128 g, 0.9 mmol) was added dropwise to the reaction mixture at 0 ° C., followed by stirring at room temperature for 10 hours. The reaction mixture was quenched with saturated NH 4 Cl solution (20 mL) and extracted with ethyl acetate (3 × 30 mL). The resulting extract was washed with water (30 mL), dried over MgSO 4 , and the solvent was evaporated under reduced pressure. Flash chromatography on silica gel using hexanes / ethyl acetate (5: 1) gave oily compound 12 (0.163 g, 76%).

1 H NMR (300 MHz, CDCl 3 ) δ 7.50-7.44 (2H, m), 7.23-7.12 (2H, m), 6.97 (2H, s), 6.92 (1H, br s), 3.85 (6H, s) , 2.06 (3H, s);

13 C NMR (75 MHz, CDCl 3 ) δ 158.5, 156.7, 154.9, 129.2, 128.6, 124.1, 122.9, 120.7, 115.0, 111.1, 100.9, 100.4, 55.8, 8.4;

HRMS m / z (M + ) calcd for C 17 H 16 O 3 : 268.1099. Found: 268.1096.

Example 4 Stemofuran C Synthesis

Reaction obtained by adding compound 12 (0.134 g, 0.5 mmol) prepared previously at 0 ° C. to a solution of boron tribromide (0.6 mL, 1.0 M in CH 2 Cl 2 , 0.6 mmol) in methylene chloride (10 mL). The mixture was stirred at 0 ° C for 10 h. Ice water (20 mL) was added to the reaction mixture, which was then extracted with methylene chloride (3 × 30 mL), washed with water and dried over anhydrous sodium sulfate. After solvent removal, compound 3 (0.111 g, 92%) was obtained by flash chromatography on silica gel using hexanes / ethyl acetate (3: 1).

mp 195-196 ° C;

1 H NMR (300 MHz, acetone- d 6 ) δ 7.59 (1H, d, J = 8.1 Hz), 7.50 (1H, d, J = 8.1 Hz), 7.27-7.22 (2H, m), 7.03 (1H, s), 6.99 (2H, s), 2.14 (3H, s);

13 C NMR (75 MHz, acetone- d 6 ) δ 157.5, 157.3, 155.5, 100.1, 129.1, 124.9, 123.8, 121.7, 113.0, 111.5, 104.1, 101.4, 8.7;

IR (KBr) 3597, 2926, 2855, 1623, 1601, 1577, 1522, 1510, 1453, 1421, 1377, 1365, 1351, 1299, 1257, 1185, 1157, 1144, 1108, 1081, 1007, 961, 937, 867 cm −1 ;

HRMS m / z (M + ) calcd for C 15 H 12 O 3 : 240.0786. Found: 240.0788.

Example 5 Synthesis of Compound 17

Ethylenediamine diacetate (18 mg, 0.1) in a solution of stemofuran A (1) (0.113 g, 0.5 mmol) and 3-methyl-2-butenal (0.084 g, 1.0 mmol) in benzene (10 mL). mmol) was added. The reaction mixture was refluxed for 24 hours, the solvent was removed and the oily residue obtained was purified by column chromatography on silica gel to give compound 17 (0.076 g, 52%).

1 H NMR (300 MHz, CDCl 3 ) δ 7.72 (1H, dd, J = 7.5,1.5 Hz), 7.64 (1H, d, J = 7.5 Hz), 7.47-7.36 (2H, m), 7.11 (1H, s), 7.10 (1H, s), 7.04 (1H, d, J = 1.5 Hz), 6.83 (1H, d, J = 9.9 Hz), 5.82 (1H, d, J = 9.9 Hz), 5.32 (1H, brs), 1.64 (6H, s);

13 C NMR (75 MHz, CDCl 3 ) δ 155.3, 154.7, 154.2, 151.6, 130.9, 129.7, 129.1, 124.3, 122.9, 120.9, 116.3, 111.0, 110.1, 105.9, 104.4, 101.6, 76.3, 27.8;

IR (neat) 3467, 2974, 2930, 1618, 1562, 1450, 1423, 1370, 1251, 1120, 1069, 962, 900, 849, 803 cm −1 ;

HRMS m / z (M + ) calcd for C 19 H 16 O 3 : 292.1099. Found: 292.1097.

Example 6 Synthesis of Compound 18

Ethylenediamine diacetate (18 mg, 0.1 mmol) was added to a solution of stemofuran A (1) (0.113 g, 0.5 mmol) and trans-cinnamaldehyde (0.132 g, 1.0 mmol) in benzene (10 mL). It was. The reaction mixture was refluxed for 24 hours, the solvent was removed and the oily residue obtained was purified by column chromatography on silica gel to give compound 18 (0.087 g, 51%).

1 H NMR (300 MHz, CDCl 3 ) δ 7.43-7.06 (9H, m), 7.80 (1H, d, J = 10.8 Hz), 6.77 (1H, s), 6.76 (1H, s), 5.79 (1H, d, J = 3.6 Hz), 5.71 (1H, dd, J = 10.8,3.6 Hz), 5.21 (1H, br s);

13 C NMR (75 MHz, CDCl 3 ) δ 155.1, 154.7, 154.3, 151.6, 140.4, 131.3, 129.0, 128.7, 128.4, 127.1, 124.4, 123.6, 122.9, 120.9, 118.1, 111.0, 110.2, 105.6, 104.7, 101.9 , 76.9;

IR (neat) 2923, 2855, 1626, 1569, 1450, 1357, 1257, 1079, 803, 747 cm −1 ;

HRMS m / z (M + ) calcd for C 23 H 16 O 3 : 340.1099. Found: 340.1096.

Example 7 Synthesis of Compound 19

Ethylenediamine diacetate (18 mg, 0.1 mmol) was added to a solution of stemofuran A (1) (0.113 g, 0.5 mmol) and citral (0.152 g, 1.0 mmol) in benzene (10 mL). The reaction mixture was refluxed for 24 hours, the solvent was removed and the oily residue obtained was purified by column chromatography on silica gel to give compound 19 (0.123 g, 68%).

1 H NMR (300 MHz, CDCl 3 ) δ 7.46 (1H, d, J = 7.0 Hz), 7.38 (1H, d, J = 7.5 Hz), 7.20-7.12 (2H, m), 6.84 (2H, s) , 6.76 (1H, s), 6.61 (1H, d, J = 9.9 Hz), 5.52 (1H, d, J = 9.9 Hz), 5.03 (1H, t, J = 6.6 Hz), 2.12-2.01 (2H, m), 1.78-1.60 (2H, m), 1.58 (3H, s), 1.51 (3H, s), 1.34 (3H, s);

13 C NMR (75 MHz, CDCl 3 ) δ 155.3, 154.6, 154.4, 151.6, 131.7, 130.8, 129.1, 128.7, 124.2, 124.0, 122.8, 120.8, 116.7, 111.0, 110.0, 105.7, 104.3, 101.6, 78.6, 41.0 , 26.2, 25.6, 22.7, 17.6;

IR (neat) 3410, 3061, 2969, 2823, 1618, 1562, 1449, 1357, 1253, 1157, 1085, 962, 908, 849, 801, 747 cm −1 ;

HRMS m / z (M + ) calcd for C 24 H 24 O 3 : 360.1725. Found: 360.1727.

Comparative Example 1

In order to evaluate whether the conditions such as the catalyst and the solvent used in the present embodiment are preferable for the synthesis of the compound, the compound 17 is synthesized in the same manner as the synthesis method of the compound 17 synthesized in Example 5, but the catalyst, It synthesize | combined by changing some conditions, such as a solvent.

Reaction catalyst Reaction condition Yield (%) One InCl 3 (20 mol%) Acetonitrile, reflux, 12 h 0 2 Yb (OTf) 3 (20 mol%) Acetonitrile, reflux, 12 h 0 3 Ca (OH) 2 (20 mol%) Methanol, reflux, 12 h 0 4 Pyridine (excess) 140 ℃, 24 hours 0 5 EDDA (20 mol%) Xylene, reflux, 24 hours 30 6 EDDA (20 mol%) Benzene, reflux, 24 hours 52

As a result, when compound 17 was synthesized through reflux reaction in a benzene or xylene solvent for 24 hours using EDDA as a catalyst, compound 17 could be synthesized in high yield. On the other hand, Compound 17 could not be obtained when different catalyst types were used or refluxing under different solvents.

While the present invention has been particularly shown and described with reference to specific embodiments thereof, those skilled in the art will appreciate that such specific embodiments are merely preferred embodiments and that the scope of the present invention is not limited thereby. something to do. It is therefore intended that the scope of the invention be defined by the claims appended hereto and their equivalents.

Claims (5)

Suzuki coupling reaction between 2-benzofuran boronic acid and 3,5-dimethoxybromobenzene in the presence of Pd (PPh 3 ) 4 was used to synthesize 2- (3,5-dimethoxyphenyl) benzofuran. Stemofuran or a derivative thereof. The method according to claim 1, wherein the synthesis method is a 2- (3,5-dimethoxyphenyl by performing a Suzuki coupling reaction between 2-benzofuran boronic acid and 3,5-dimethoxybromobenzene in the presence of Pd (PPh 3 ) 4 Synthesizing benzofuran; And demethylating the methyl group of 2- (3,5-dimethoxyphenyl) benzofuran to synthesize stemofuran A of formula (I):
[Formula 1]
Figure pat00005
 The method according to claim 2, further comprising the step of reacting the stemofuran A with α, β-unsaturated aldehyde in the presence of ethylenediamine diacetate to synthesize a stemofuran derivative of the formula (2) Or a method for synthesizing derivatives thereof:
(2)
Figure pat00006

In Formula 2, R 1 is selected from hydrogen or methyl group, R 2 is selected from methyl group, benzyl group or prenyl group. The method of claim 3, wherein the α, β-unsaturated aldehyde is any one selected from the group consisting of 3-methyl-2-butenal, trans-cinnamaldehyde and citral stemofuran or derivatives thereof. The method according to claim 1, wherein the synthesis method is a 2- (3,5-dimethoxyphenyl by performing a Suzuki coupling reaction between 2-benzofuran boronic acid and 3,5-dimethoxybromobenzene in the presence of Pd (PPh 3 ) 4 Synthesizing benzofuran; Adding n-BuLi to the 2- (3,5-dimethoxyphenyl) benzofuran, and then adding methyl iodide to synthesize 2- (3,5-dimethoxy-4-methylphenyl) benzofuran ; And demethylating a part of the methyl group of 2- (3,5-dimethoxy-4-methylphenyl) benzofuran to synthesize stemofuran C of formula (3). Derivative synthesis method:
(3)
Figure pat00007
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