JPS6043066B2 - 2,3-dihydroindolizin-2-one derivative and its production method - Google Patents
2,3-dihydroindolizin-2-one derivative and its production methodInfo
- Publication number
- JPS6043066B2 JPS6043066B2 JP55030693A JP3069380A JPS6043066B2 JP S6043066 B2 JPS6043066 B2 JP S6043066B2 JP 55030693 A JP55030693 A JP 55030693A JP 3069380 A JP3069380 A JP 3069380A JP S6043066 B2 JPS6043066 B2 JP S6043066B2
- Authority
- JP
- Japan
- Prior art keywords
- formulas
- general formula
- lower alkyl
- alkyl group
- dihydroindolizin
- 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
Links
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
【発明の詳細な説明】
本発明は一般式
２（１）
Ｒ、
式中Ｒは水素原子、低級アルキル基又はフェニル基を、
Ｒ、およびＲ２は水素原子又は低級アルキ”ル基を意味
する）で示される新規な２、３−ジヒドロインドリジン
ー２−オン誘導体およびその製法に関するものである。Detailed Description of the Invention The present invention is based on the general formula 2(1) R, where R represents a hydrogen atom, a lower alkyl group, or a phenyl group,
The present invention relates to a novel 2,3-dihydroindolizin-2-one derivative represented by R and R2 each representing a hydrogen atom or a lower alkyl group, and a method for producing the same.
従来、一般式（１）で示される２、３−ジヒドロインド
リジンー２−オン誘導体については全く知ら、れていな
かつた。本発明者らはこの種の２、３−ジヒドロインド
リジン誘導体について鋭意研究を重ねた結果、本発明を
完成するに至つた。本発明の化合物は上記一般式（１）
で表わされる２，３−ジヒドロインドリジンー２−オン
誘導体であり、この化合物は文献未載の新記化合物であ
る。Hitherto, the 2,3-dihydroindolizin-2-one derivative represented by the general formula (1) has not been known at all. The present inventors have conducted extensive research on this type of 2,3-dihydroindolizine derivatives, and as a result, have completed the present invention. The compound of the present invention has the above general formula (1)
It is a 2,3-dihydroindolizin-2-one derivative represented by the following formula, and this compound is a new compound that has not been described in any literature.
本発明の化合物は抗菌作用を有し、医薬として有用であ
る。The compounds of the present invention have antibacterial activity and are useful as medicines.
一般式（１）で示される本発明の化合物において置換基
である低級アルキル基としてはメチル、エチル、ブチル
、ヘキシル等の炭素数１〜６のアルキル基を例示するこ
とができる。Examples of the lower alkyl group which is a substituent in the compound of the present invention represented by general formula (1) include alkyl groups having 1 to 6 carbon atoms such as methyl, ethyl, butyl, and hexyl.
一般式（１）で示される化合物は例えば一般式（式様Ｒ
ｓＲｌおよびＲ２は前記の意味を有し、Ｒ３は低級アル
キル基を、Ｘはハロゲン原子を意味する。The compound represented by the general formula (1) is, for example, the general formula (formula form R
sRl and R2 have the above meanings, R3 represents a lower alkyl group, and X represents a halogen atom.
）で示される化合物を塩基性物質の存在下、閉環縮合す
ることによつて得られる。) can be obtained by ring-closing condensation of the compound shown in (1) in the presence of a basic substance.
上記一般式（２）の置換基Ｒ３の低級アルキル基の例と
しては炭素数１〜６のアルキル基、例えばメチル、エチ
ル、ブチル、ヘキシル等が、Ｘのハロゲンとしては、、
塩素、臭素、沃素原子等が挙げられる。Examples of the lower alkyl group for the substituent R3 in the above general formula (2) are alkyl groups having 1 to 6 carbon atoms, such as methyl, ethyl, butyl, hexyl, etc., and the halogen for X is,
Examples include chlorine, bromine, and iodine atoms.
上記一般式（２）の化合物は公知の化合物であり、例え
ばジャーナル．オブ．オーガニック．ケミス．トリー（
Ｊ．Ｏｒｇ，Ｃｈｅｍ）３６，２４５１（１９７１）に
記載の方法又はこれに準する方法により容易に得られる
。The compound of general formula (2) above is a known compound, for example, as described in Journal. of. organic. Chemis. Tory (
J. Org, Chem) 36, 2451 (1971) or a method analogous thereto.
本発明の反応は通常不活性溶媒中で行うのが好ましい。
用いられる不活性溶媒としては例えば、メタノール、エ
タノール、プロパノール等の低級アルコール類、ジオキ
サン、テトラヒドロフラン等のエーテル類、ジメチルス
ルホキシド等の極性溶媒類が用いられる。塩基性物質と
しては例えば、水酸化ナトリウム、水酸化カリウム、炭
酸ナトリウム、炭酸カリウム等が用いられる。塩基性物
質は過剰使用してもよいが、通常化合物（２）に対して
等モル量程度使用するのが好ましい。反応ノ温度は原料
の種類、溶媒の種類等により必ずしも一定ではないが通
常室温付近が好適に用いられる。本発明の一般式（１）
で示される２，３−ジヒドロインドリジンー２−オン誘
導体は通常公知の精製法、例えば抽出、濃縮、蒸留、カ
ラムクロマトグラフィー再結晶等の手段により容易に精
製、分離される次に実施例を挙げて、本発明を具体的に
説明するが、これはその一例に過ぎないものであつて、
何らこれのみに限定されるものではない。The reaction of the present invention is usually preferably carried out in an inert solvent.
Examples of the inert solvent used include lower alcohols such as methanol, ethanol, and propanol, ethers such as dioxane and tetrahydrofuran, and polar solvents such as dimethyl sulfoxide. As the basic substance, for example, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, etc. are used. Although the basic substance may be used in excess, it is usually preferable to use it in an equimolar amount to compound (2). Although the reaction temperature is not necessarily constant depending on the type of raw materials, the type of solvent, etc., a temperature around room temperature is usually suitably used. General formula (1) of the present invention
The 2,3-dihydroindolizin-2-one derivative represented by is easily purified and separated by commonly known purification methods, such as extraction, concentration, distillation, column chromatography and recrystallization. The present invention will be specifically explained by referring to the following, but this is only one example, and
It is not limited to this in any way.
実施例１
２−ベンジルー１−（エトキシカルボニルメチル）ピリ
ジニウムプロミド３．３６ｇ（１０ミリモル）をエタノ
ール１００ｍ１に溶解し、これに水酸化カリウム水溶液
（水酸化カリウム０．６２ｇ１水２ｍｔ）を滴下した後
、室温下で５分間攪拌する。Example 1 3.36 g (10 mmol) of 2-benzyl-1-(ethoxycarbonylmethyl)pyridinium bromide was dissolved in 100 ml of ethanol, and an aqueous potassium hydroxide solution (0.62 g of potassium hydroxide 1 2 mt of water) was added dropwise thereto. , stir for 5 minutes at room temperature.
反応混合液から析出した無機物を治去し、戸液を濃縮す
る。残渣をアルミナカラムを用いて分離後、クロロホル
ム−ヘキサンから再結晶すると融点１３６〜１３８℃の
１−フェニルー２，３−ジヒドロインドリジンー２−オ
ンー１．６８ｇが得られる（収率７４％）。実施例２
実施例１と同様の方法により下記表１の化合物を合成し
た。The inorganic substances precipitated from the reaction mixture are removed, and the solution is concentrated. The residue is separated using an alumina column and then recrystallized from chloroform-hexane to obtain 1.68 g of 1-phenyl-2,3-dihydroindolizin-2-one having a melting point of 136-138°C (yield 74%). Example 2 The compounds shown in Table 1 below were synthesized in the same manner as in Example 1.
Claims (1)
、Ｒ＿１およびＲ＿２は水素原子又は低級アルキル基を
意味する）で示される２，３−ジヒドロインドリジン−
２−オン誘導体。 ２ 一般式 ▲数式、化学式、表等があります▼ （式中Ｒは水素原子、低級アルキル基又はフェニル基を
、Ｒ＿１およびＲ＿２は水素原子または低級アルキル基
を、Ｒ＿３は低級アルキル基、Ｘはハロゲン原子を意味
する）で示される化合物を塩基性物質の存在下に閉環縮
合させることを特徴とする一般式▲数式、化学式、表等
があります▼ （式中Ｒ、Ｒ＿１およびＲ＿２は前記と同一の意味を有
する）で示される２，３−ジヒドロインドリジン−２−
オン誘導体の製法。[Claims] 1 General formula ▲ Numerical formulas, chemical formulas, tables, etc. 2,3-dihydroindolizine-
2-one derivative. 2 General formula▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, R is a hydrogen atom, a lower alkyl group, or a phenyl group, R_1 and R_2 are a hydrogen atom or a lower alkyl group, R_3 is a lower alkyl group, and X is a halogen. There are general formulas ▲ mathematical formulas, chemical formulas, tables, etc. ▼ that are characterized by ring-closing condensation of compounds represented by (meaning atoms) in the presence of a basic substance ▼ (wherein R, R_1 and R_2 are the same as above) 2,3-dihydroindolizine-2-
Method for producing ON derivatives.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55030693A JPS6043066B2 (en) | 1980-03-10 | 1980-03-10 | 2,3-dihydroindolizin-2-one derivative and its production method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55030693A JPS6043066B2 (en) | 1980-03-10 | 1980-03-10 | 2,3-dihydroindolizin-2-one derivative and its production method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56127377A JPS56127377A (en) | 1981-10-06 |
| JPS6043066B2 true JPS6043066B2 (en) | 1985-09-26 |
Family
ID=12310751
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP55030693A Expired JPS6043066B2 (en) | 1980-03-10 | 1980-03-10 | 2,3-dihydroindolizin-2-one derivative and its production method |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6043066B2 (en) |
-
1980
- 1980-03-10 JP JP55030693A patent/JPS6043066B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56127377A (en) | 1981-10-06 |
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