JPH0813814B2 - Process for producing fused heterocyclic compound - Google Patents
Process for producing fused heterocyclic compoundInfo
- Publication number
- JPH0813814B2 JPH0813814B2 JP63262128A JP26212888A JPH0813814B2 JP H0813814 B2 JPH0813814 B2 JP H0813814B2 JP 63262128 A JP63262128 A JP 63262128A JP 26212888 A JP26212888 A JP 26212888A JP H0813814 B2 JPH0813814 B2 JP H0813814B2
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- formula
- compound represented
- tetrahydro
- general formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims description 8
- 150000002391 heterocyclic compounds Chemical class 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 10
- -1 tetrahydro-7-oxo-8-indolizinecarboxylic acid ester Chemical class 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- MBIWWPKSHKFRRK-UHFFFAOYSA-N 2-ethyl-2,6-dimethyl-1,3-dioxin-4-one Chemical compound CCC1(C)OC(C)=CC(=O)O1 MBIWWPKSHKFRRK-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- OPVZWGOKPGTGJL-UHFFFAOYSA-N O=C1C(C2=CC=CCN2CC1)C(=O)O Chemical compound O=C1C(C2=CC=CCN2CC1)C(=O)O OPVZWGOKPGTGJL-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- FMYJYRGSXCDJJP-UHFFFAOYSA-N 4-methyl-2-oxo-6,7,8,9-tetrahydroquinolizine-1-carboxylic acid Chemical compound C1CCCN2C(C)=CC(=O)C(C(O)=O)=C21 FMYJYRGSXCDJJP-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- MVQWICMCUQFVFB-UHFFFAOYSA-N methyl 2-piperidin-2-ylideneacetate Chemical compound COC(=O)C=C1CCCCN1 MVQWICMCUQFVFB-UHFFFAOYSA-N 0.000 description 1
- ORAKNQSHWMHCEY-UHFFFAOYSA-N methyl 2-pyridin-2-ylacetate Chemical compound COC(=O)CC1=CC=CC=N1 ORAKNQSHWMHCEY-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
Description
【発明の詳細な説明】 （産業上の利用分野） 本発明は、医薬、農薬等の製造中間体として有用な縮
合複素環化合物の製造法に関する。TECHNICAL FIELD The present invention relates to a method for producing a fused heterocyclic compound useful as an intermediate for the production of medicines, agricultural chemicals and the like.
（従来の技術及び発明が解決しようとする課題） 従来、式（III）で示されるテトラヒドロ‐7-オキソ
‐8-インドリジンカルボン酸エステル（ｎ＝３）又はテ
トラヒドロ‐2-オキソ‐2H-キノリジン‐1-カルボン酸
エステル（ｎ＝４）としては、1,2,3,7-テトラヒドロ‐
5-メチル‐7-オキソ‐8-インドリジンカルボン酸エチル
（薬学雑誌，93,1084（1973））及び6,7,8,9-テトラヒ
ドロ‐4-メチル‐2-オキソ‐2H-キノリジン‐1-カルボ
ン酸メチル（Monatsh.Chem.,100,136（1969））が知ら
れている。前者の化合物は、エチルα‐（テトラヒドロ
‐2-ピロリジニリデン）アセテートとジケテンとの反応
によって得られているが、収率は63％であり、工業的製
法としては満足できるものではない。又、後者の化合物
は、2-ピリジル酢酸メチルとジケテンとの反応によって
得られる4-メチル‐2-オキソ‐2H-キノリジン‐1-カル
ボン酸メチルを水素化することによって得られている
が、前段の反応収率が低く工業的製法とはいえない。(Prior Art and Problems to be Solved by the Invention) Conventionally, tetrahydro-7-oxo-8-indolizinecarboxylic acid ester (n = 3) or tetrahydro-2-oxo-2H-quinolidine represented by the formula (III) -1-carboxylic acid ester (n = 4) includes 1,2,3,7-tetrahydro-
5-methyl-7-oxo-8-indolizine-carboxylate (Pharmaceutical Journal, 93, 1084 (1973)) and 6,7,8,9-tetrahydro-4-methyl-2-oxo -2H- quinolizine -1 -Methyl carboxylate (Monatsh. Chem., 100 , 136 (1969)) is known. The former compound is obtained by the reaction of ethyl α- (tetrahydro-2-pyrrolidinylidene) acetate with diketene, but the yield is 63%, which is not satisfactory as an industrial production method. The latter compound was obtained by hydrogenating methyl 4-methyl-2-oxo-2H-quinolizine-1-carboxylate obtained by the reaction of methyl 2-pyridylacetate and diketene. The reaction yield is low and cannot be said to be an industrial production method.
この発明は、テトラヒドロ‐7-オキソ‐8-インドリジ
ンカルボン酸エステル誘導体及びテトラヒドロ‐2-オキ
ソ‐2H-キノリジン‐1-カルボン酸エステル誘導体を工
業的に好収率で製造する方法を提供することを目的とす
る。The present invention provides a method for industrially producing a tetrahydro-7-oxo-8-indolizinecarboxylic acid ester derivative and a tetrahydro-2-oxo-2H-quinolizine-1-carboxylic acid ester derivative in good yield. With the goal.
（課題を解決するための手段） この発明は、一般式（Ｉ）又は（Ｉ′）： ［式中（Ｉ）又は（Ｉ′）中R1は低級アルキル基又はフ
ェニル基;nは３又は４を意味する。］で表される化合物
と一般式（II）： ［式中R2は低級アルキル基；R3，R4は水素原子，アルキ
ル基，フェニル基又はR3およびR4がR3とR4の結合する炭
素原子と共にシクロアルキル基を形成してもよい。］で
表される化合物とを反応させることを特徴とする一般式
（III）： ［式中R1，R2,nは上記と同じ］で表される縮合複素環化
合物の製造法に関する。(Means for Solving the Problem) The present invention provides a compound represented by the general formula (I) or (I ′): [In the formula (I) or (I ′), R 1 is a lower alkyl group or a phenyl group; n is 3 or 4]. ] And the compound represented by the general formula (II): [Wherein R 2 is a lower alkyl group; R 3 , R 4 are a hydrogen atom, an alkyl group, a phenyl group or R 3 and R 4 may form a cycloalkyl group together with the carbon atom to which R 3 and R 4 are bonded. Good. ] The compound represented by the general formula (III): The present invention relates to a method for producing a fused heterocyclic compound represented by the formula [wherein R 1 , R 2 , and n are the same as above].
原料として用いる式（Ｉ）又は（Ｉ′）の化合物は従
来既知の方法で製造することができる。式（Ｉ）と式
（Ｉ′）は互変異性体を表す。式（Ｉ）又は（Ｉ′）に
おけるR1は低級アルキル基又はフェニル基である。低級
アルキル基としては、メチル、エチル、プロピル、イソ
プロピル、ブチル、イソブチル、第３ブチル、イソペン
チル等が挙げられる。ｎは３又は４を意味し、それぞれ
生成物としてテトラヒドロ‐7-オキソ‐8-インドリジン
カルボン酸エステル誘導体及びテトラヒドロ‐2-オキソ
‐2H-キノリジン‐1-カルボン酸エステル誘導体を与え
る。一般式（II）の化合物も従来既知の方法で製造する
ことができる。式（II）におけるR2は低級アルキル基を
表し、例えば、メチル、エチル、プロピル、イソプロピ
ル、ブチル、イソブチル、第３ブチル、イソペンチル等
が挙げられる。式（II）におけるR3とR4が目的物に導入
されない基であり、入手容易で安価なものを選択利用す
るのが望ましい。R3とR4としてメチル基又はエチル基が
特に好ましい。The compound of formula (I) or (I ') used as a starting material can be produced by a conventionally known method. Formula (I) and formula (I ') represent tautomers. R 1 in formula (I) or (I ′) is a lower alkyl group or a phenyl group. Examples of the lower alkyl group include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, isopentyl and the like. n means 3 or 4 and gives a tetrahydro-7-oxo-8-indolizinecarboxylic acid ester derivative and a tetrahydro-2-oxo-2H-quinolizine-1-carboxylic acid ester derivative, respectively, as products. The compound of the general formula (II) can also be produced by a conventionally known method. R 2 in the formula (II) represents a lower alkyl group, and examples thereof include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, isopentyl and the like. R 3 and R 4 in the formula (II) are groups that are not introduced into the desired product, and it is desirable to select and use easily available and inexpensive groups. A methyl group or an ethyl group is particularly preferable as R 3 and R 4 .
この発明における反応は無溶媒下又は不活性溶媒中で
行うことが出来る。好ましい溶媒の例としてベンゼン、
トルエン、キシレン、テトラリン、デカリン、ジフェニ
ルエーテルなどが挙げられる。反応温度としては、一般
式（II）で表される化合物の熱分解温度を目安として、
約100℃から200℃程度の温度が用いられる。The reaction in the present invention can be carried out without solvent or in an inert solvent. Benzene as an example of a preferred solvent,
Examples thereof include toluene, xylene, tetralin, decalin and diphenyl ether. As the reaction temperature, using the thermal decomposition temperature of the compound represented by the general formula (II) as a guide,
Temperatures on the order of about 100 ° C to 200 ° C are used.
また、一般式（II）で表される化合物の使用量は、一
般式（Ｉ）又は（Ｉ′）で表される化合物に対して１当
量以上、好ましくは1.2〜3.0当量の範囲である。The amount of the compound represented by the general formula (II) used is 1 equivalent or more, preferably 1.2 to 3.0 equivalents, relative to the compound represented by the general formula (I) or (I ′).
この反応においては熱分解生成物として式（IV）： で表されるカルボニル化合物が反応系中に発生する。こ
の化合物の沸点が反応設定温度より低い場合には、系外
に留出しながら反応を行うことが有利である。In this reaction, the thermal decomposition product is represented by the formula (IV): A carbonyl compound represented by is generated in the reaction system. When the boiling point of this compound is lower than the set reaction temperature, it is advantageous to carry out the reaction while distilling it out of the system.
反応後の精製法は特に限定されないが、通常反応混合
物を室温まで放冷することによって生ずる結晶をろ過す
るだけで、容易に目的物を得ることができ、工業的に非
常に有利である。The purification method after the reaction is not particularly limited, but usually the desired product can be easily obtained only by filtering the crystals generated by allowing the reaction mixture to cool to room temperature, which is industrially very advantageous.
以下実施例を挙げて本発明を更に詳しく説明する。 Hereinafter, the present invention will be described in more detail with reference to examples.
（実施例） 実施例１ メチルα‐（テトラヒドロ‐2-ピロリジニリデン）ア
セテート1.41g,2-エチル‐2,6-ジメチル‐4H-1,3-ジオ
キシン‐4-オン3.90g及びキシレン10mlの混合物を油浴
温度140℃で２時間加熱撹はんした。その間に副生する
メチルエチルケトンはディーンスターク装置により系外
に除去した。反応混合物を室温まで放冷し、生じた結晶
をろ別、洗浄し、減圧下で乾燥すると1,2,3,7-テトラヒ
ドロ‐5-メチル‐7-オキソ‐8-インドリジンカルボン酸
メチルが1.86g（収率90％）得られた。Example 1 A mixture of 1.41 g of methyl α- (tetrahydro-2-pyrrolidinylidene) acetate, 3.90 g of 2-ethyl-2,6-dimethyl-4H-1,3-dioxin-4-one and 10 ml of xylene was added. The mixture was heated with stirring at an oil bath temperature of 140 ° C for 2 hours. During that time, methyl ethyl ketone produced as a by-product was removed to the outside of the system by the Dean Stark apparatus. The reaction mixture is allowed to cool to room temperature, the resulting crystals are filtered off, washed and dried under reduced pressure to give methyl 1,2,3,7-tetrahydro-5-methyl-7-oxo-8-indolizinecarboxylate. 1.86 g (yield 90%) was obtained.
融点:125.5-132℃ IR（KBrディスク）:1637,1700cm-1 NMR（CDCl3）δ値： 1.90-2.65（m,2H）,2.23（s,3H）,3.28（t,2H）,3.81
（s,3H）,4.01（t,2H）,6.15（s,1H）。Melting point: 125.5-132 ° C IR (KBr disk): 1637,1700cm -1 NMR (CDCl 3 ) δ value: 1.90-2.65 (m, 2H), 2.23 (s, 3H), 3.28 (t, 2H), 3.81
(S, 3H), 4.01 (t, 2H), 6.15 (s, 1H).
実施例２ メチルα‐（ヘキサヒドロ‐2-ピリジニリデン）アセ
テート3.10gとキシレン10mlの混合物を穏やかに還流さ
せながら、2-エチル‐2,6-ジメチル‐4H-1,3-ジオキシ
ン‐4-オン7.81gのキシレン（10ml）の溶液を20分間で
滴下し、さらに２時間加熱還流を続けた。その間に副生
するメチルエチルケトンはディーンスターク装置により
系外に除去した。反応混合物を室温まで放冷し、生じた
結晶をろ別、洗浄し、減圧下で乾燥すると6,7,8,9-テト
ラヒドロ‐4-メチル‐2-オキソ‐2H-キノリジン‐1-カ
ルボン酸メチルが4.11g（収率93％）得られた。Example 2 2-Ethyl-2,6-dimethyl-4H-1,3-dioxin-4-one 7.81 while gently refluxing a mixture of 3.10 g of methyl α- (hexahydro-2-pyridinylidene) acetate and 10 ml of xylene. A solution of g of xylene (10 ml) was added dropwise over 20 minutes and heating under reflux was continued for another 2 hours. During that time, methyl ethyl ketone produced as a by-product was removed to the outside of the system by the Dean Stark apparatus. The reaction mixture was allowed to cool to room temperature, the resulting crystals were filtered off, washed and dried under reduced pressure to give 6,7,8,9-tetrahydro-4-methyl-2-oxo-2H-quinolizine-1-carboxylic acid. 4.11 g (yield 93%) of methyl was obtained.
融点:173−177℃ IR（KBrディスク）:1635,1728cm-1 NMR（CDCl3）δ値： 1.40-2.40（m,4H）,2.27（s,3H）,2.77（t,2H）,3.80
（t,2H）,3.82（s,3H）,6.17（s,1H）。Melting point: 173-177 ° C IR (KBr disc): 1635, 1728 cm -1 NMR (CDCl 3 ) δ value: 1.40-2.40 (m, 4H), 2.27 (s, 3H), 2.77 (t, 2H), 3.80
(T, 2H), 3.82 (s, 3H), 6.17 (s, 1H).
Claims (1)
ェニル基;nは３又は４を意味する。］で表される化合物
と一般式（II）： ［式中R2は低級アルキル基；R3，R4は水素原子，アルキ
ル基，フェニル基又はR3およびR4がR3とR4の結合する炭
素原子と共にシクロアルキル基を形成してもよい。］で
表される化合物とを反応させることを特徴とする一般式
（III）： ［式中R1，R2,nは上記と同じ］で表される縮合複素環化
合物の製造法。1. General formula (I) or (I '): [In the formula (I) or (I ′), R 1 is a lower alkyl group or a phenyl group; n is 3 or 4]. ] And the compound represented by the general formula (II): [Wherein R 2 is a lower alkyl group; R 3 , R 4 are a hydrogen atom, an alkyl group, a phenyl group or R 3 and R 4 may form a cycloalkyl group together with the carbon atom to which R 3 and R 4 are bonded. Good. ] The compound represented by the general formula (III): A process for producing a fused heterocyclic compound represented by [wherein R 1 , R 2 and n are the same as above].
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63262128A JPH0813814B2 (en) | 1988-10-18 | 1988-10-18 | Process for producing fused heterocyclic compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63262128A JPH0813814B2 (en) | 1988-10-18 | 1988-10-18 | Process for producing fused heterocyclic compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02108691A JPH02108691A (en) | 1990-04-20 |
| JPH0813814B2 true JPH0813814B2 (en) | 1996-02-14 |
Family
ID=17371441
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63262128A Expired - Lifetime JPH0813814B2 (en) | 1988-10-18 | 1988-10-18 | Process for producing fused heterocyclic compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0813814B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7426625B2 (en) | 2004-03-31 | 2008-09-16 | International Business Machines Corporation | Data processing system and computer program product for support of system memory addresses with holes |
-
1988
- 1988-10-18 JP JP63262128A patent/JPH0813814B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH02108691A (en) | 1990-04-20 |
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