JPS6228151B2 - - Google Patents
Info
- Publication number
- JPS6228151B2 JPS6228151B2 JP4245980A JP4245980A JPS6228151B2 JP S6228151 B2 JPS6228151 B2 JP S6228151B2 JP 4245980 A JP4245980 A JP 4245980A JP 4245980 A JP4245980 A JP 4245980A JP S6228151 B2 JPS6228151 B2 JP S6228151B2
- Authority
- JP
- Japan
- Prior art keywords
- general formula
- lower alkyl
- alkyl group
- hydrogen atom
- 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
Links
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
【発明の詳細な説明】
本発明は新規なピラノ〔２，３−ｂ〕インドリ
ジン誘導体およびその製法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel pyrano[2,3-b]indolizine derivative and a method for producing the same.
本発明のピラノ〔２，３−ｂ〕インドリジン誘
導体は一般式
（式中Ｒは水素原子、低級アルキル基またはフ
エニル基を、R1は水素原子または低級アルキル
基を意味する）で示される化合物である。 The pyrano[2,3-b]indolizine derivative of the present invention has the general formula (In the formula, R represents a hydrogen atom, a lower alkyl group, or a phenyl group, and R 1 represents a hydrogen atom or a lower alkyl group.)
従来、一般式(1)で示されるピラノ〔２，３−
ｂ〕インドリジン誘導体はこれまで全く知られて
いなかつた。本発明者はこの種のピラノインドリ
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。 Conventionally, pyrano[2,3-
b] Indolizine derivatives were completely unknown until now. The present inventor has completed the present invention as a result of intensive research on this type of pyranoindolizine derivative.
本発明の化合物は上記一般式(1)で表わされるピ
ラノ〔２，３−ｂ〕インドリジン誘導体であり、
文献未載の新規化合物である。 The compound of the present invention is a pyrano[2,3-b]indolizine derivative represented by the above general formula (1),
This is a new compound that has not been published in any literature.
本発明の化合物は降圧作用、抗アレルギー作
用、抗腫瘍作用、抗菌作用等を有し医薬として有
用である。 The compound of the present invention has antihypertensive action, antiallergic action, antitumor action, antibacterial action, etc., and is useful as a medicine.
本発明の一般式(1)で示される化合物は例えば一
般式
（式中R2は低級アルキル基を、Ｘはハロゲン
原子を、ＲおよびR1は前記の意味を有する）で
示される化合物と一般式
Ｘ−（CH2）3−Ｘ (3)
（式中Ｘは前記の意味を有する）で示される化
合物とを反応させることによつて得られる。 The compound represented by the general formula (1) of the present invention is, for example, a compound represented by the general formula (1) (In the formula, R 2 is a lower alkyl group, X is a halogen atom, and R and R 1 have the above-mentioned meanings.) X has the above-mentioned meaning).
上記一般式(1)，(2)あるいは(3)におけるＲ，R1
およびR2で示された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、プロピル、ブチル、ペンチル、ヘキシル基
が、Ｘで示されるハロゲン原子としては、例えば
塩素、臭素、沃素原子等が挙げられる。 R, R 1 in the above general formula (1), (2) or (3)
Examples of lower alkyl groups represented by R2 include alkyl groups having 1 to 6 carbon atoms, such as methyl, ethyl, propyl, butyl, pentyl, and hexyl groups; examples of halogen atoms represented by X include chlorine, Examples include bromine and iodine atoms.
本発明の反応は通常、不活性溶媒中、塩基性物
質の存在下で行うのが好ましい。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
物質の使用量は適宜選択できるが、通常一般式(3)
で示される化合物に対して約２〜３倍モル量程度
を用いるのが好ましい。反応温度は原料の種類、
溶媒の種類等により必ずしも、一定ではないが通
常室温付近が好ましい。 The reaction of the present invention is usually preferably carried out in an inert solvent in the presence of a basic substance. Examples of the inert solvent used include lower alcohols such as methanol, ethanol, and propanol, ethers such as dioxane and tetrahydrofuran, and dimethyl sulfoxide. As the basic substance, for example, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, etc. are used. The amount of basic substance used can be selected as appropriate, but usually the general formula (3)
It is preferable to use about 2 to 3 times the molar amount of the compound represented by. The reaction temperature depends on the type of raw materials,
Although it is not necessarily constant depending on the type of solvent, etc., a temperature around room temperature is usually preferable.
本発明の方法において用いられる一般式(2)で示
される原料化合物は公知の化合物であり、例えば
ジヤーナル・オブ・オーガニツク・ケミストリ
ー、36，2451（1971）に記載の方法またはこれに
準ずる方法によつて容易に得られる。また一般式
(3)で示される化合物も入手容易な公知化合物であ
る。一般式(2)及び(3)で示される化合物の使用割合
は適宜に決定できるが、通常等モル程度用いるの
が好ましい。 The raw material compound represented by general formula (2) used in the method of the present invention is a known compound, and can be prepared, for example, by the method described in Journal of Organic Chemistry, 36 , 2451 (1971) or a method analogous thereto. It is easily obtained. Also general formula
The compound represented by (3) is also a known compound that is easily available. The proportion of the compounds represented by formulas (2) and (3) to be used can be determined as appropriate, but it is usually preferable to use equimolar amounts.
本発明の化合物は通常公知の方法により精製す
ることができ、例えば抽出、濃縮、蒸留、カラム
クロマトグラフイー、再結晶等により容易に精製
することができる。 The compound of the present invention can be purified by generally known methods, such as extraction, concentration, distillation, column chromatography, recrystallization, etc.
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。 Next, the present invention will be specifically explained with reference to Examples, but these are merely examples and are not limited to these in any way.
実施例 １
２−ベンジル−１−（エトキシカルボニルメチ
ル）ピリジニウムブロミド3.36ｇ（10ミリモ
ル）、１，３−ジブロムプロパン2.17ｇ（11ミリ
モル）をエタノール100mlに溶解し、これに水酸
化カリウム水溶液（水酸化カリウム1.96ｇ、水５
ml）を加えた後、室温下で一晩撹拌する。この反
応混合液に希塩酸を加えて中和し、析出した無機
物を去し、液を濃縮する。残渣をアルミナカ
ラムを用いて分離後、エチルエーテル−ヘキサン
から再結晶すると融点154〜156℃の10−フエニル
−３，４−ジヒドロ−2H−ピラノ〔２，３−
ｂ〕インドリジン1.05ｇが得られる（収率42
％）。Example 1 3.36 g (10 mmol) of 2-benzyl-1-(ethoxycarbonylmethyl)pyridinium bromide and 2.17 g (11 mmol) of 1,3-dibromopropane were dissolved in 100 ml of ethanol, and a potassium hydroxide aqueous solution ( Potassium hydroxide 1.96g, water 5
ml) and stir overnight at room temperature. Dilute hydrochloric acid is added to the reaction mixture to neutralize it, the precipitated inorganic substances are removed, and the solution is concentrated. After separating the residue using an alumina column, recrystallization from ethyl ether-hexane yields 10-phenyl-3,4-dihydro-2H-pyrano[2,3-
b] 1.05 g of indolizine is obtained (yield: 42
%).
元素分析（C17H15NOとして）
Ｃ Ｈ Ｎ
計算値（％） 81.90 6.06 5.62
実測値（％） 81.68 6.15 5.61
実施例 ２
２−エチル−１−（エトキシカルボニルメチ
ル）ピリジニウムブロミド2.74ｇ（10ミリモ
ル）、１，３−ジクロルプロパン1.24ｇ（11ミリ
モル）をエタノール100mlに溶解し、これに水酸
化カリウム水溶液（水酸化カリウム1.96ｇ、水５
ml）を加えた後、室温下で一晩撹拌する。この反
応混合液に希塩酸を加えて中和し、析出した無機
物を去し、液を濃縮する。残渣をアルミナカ
ラムを用いて分離すると油状物の10−メチル−
３，４−ジヒドロ−2H−ピラノ〔２，３−ｂ〕
インドリジンが得られる。Elemental analysis (as C 17 H 15 NO) C H N Calculated value (%) 81.90 6.06 5.62 Actual value (%) 81.68 6.15 5.61 Example 2 2-ethyl-1-(ethoxycarbonylmethyl)pyridinium bromide 2.74 g (10 mmol) ), 1.24 g (11 mmol) of 1,3-dichloropropane was dissolved in 100 ml of ethanol, and an aqueous solution of potassium hydroxide (1.96 g of potassium hydroxide, 5 g of water) was dissolved in 100 ml of ethanol.
ml) and stir overnight at room temperature. Dilute hydrochloric acid is added to the reaction mixture to neutralize it, the precipitated inorganic substances are removed, and the solution is concentrated. When the residue is separated using an alumina column, 10-methyl-
3,4-dihydro-2H-pyrano[2,3-b]
Indolizine is obtained.
融点141〜143℃（ピクレート） 元素分析（C18H16N4O8として） Ｃ Ｈ Ｎ 計算値（％） 51.92 3.87 13.46 実測値（％） 51.91 3.95 13.39Melting point 141-143℃ (picrate) Elemental analysis (as C 18 H 16 N 4 O 8 ) C H N Calculated value (%) 51.92 3.87 13.46 Actual value (%) 51.91 3.95 13.39
Claims (1)
エニル基を、R1は水素原子または低級アルキル
基を意味する）で示されるピラノ〔２，３−ｂ〕
インドリジン誘導体。 ２ 一般式 （式中Ｒは水素原子、低級アルキル基またはフ
エニル基を、R1は水素原子または低級アルキル
基を、R2は低級アルキル基を、Ｘはハロゲン原
子を意味する）で示される化合物と一般式 Ｘ−（CH2）3−Ｘ （式中Ｘは前記の意味を有する） で示される化合物とを反応させることを特徴とす
る一般式 （式中ＲおよびR1は前記の意味を有する）で
示されるピラノ〔２，３−ｂ〕インドリジン誘導
体の製法。[Claims] 1. General formula (In the formula, R represents a hydrogen atom, a lower alkyl group, or a phenyl group, and R 1 represents a hydrogen atom or a lower alkyl group.) Pyrano[2,3-b]
Indolizine derivatives. 2 General formula (In the formula, R represents a hydrogen atom, a lower alkyl group, or a phenyl group, R 1 represents a hydrogen atom or a lower alkyl group, R 2 represents a lower alkyl group, and X represents a halogen atom) and the compound represented by the general formula A general formula characterized by reacting with a compound represented by X-(CH 2 ) 3 -X (wherein X has the above meaning) A method for producing a pyrano[2,3-b]indolizine derivative represented by the formula (wherein R and R 1 have the above-mentioned meanings).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4245980A JPS56139486A (en) | 1980-03-31 | 1980-03-31 | Pyrano 2,3-b indolizine derivative and its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4245980A JPS56139486A (en) | 1980-03-31 | 1980-03-31 | Pyrano 2,3-b indolizine derivative and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56139486A JPS56139486A (en) | 1981-10-30 |
| JPS6228151B2 true JPS6228151B2 (en) | 1987-06-18 |
Family
ID=12636649
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4245980A Granted JPS56139486A (en) | 1980-03-31 | 1980-03-31 | Pyrano 2,3-b indolizine derivative and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS56139486A (en) |
-
1980
- 1980-03-31 JP JP4245980A patent/JPS56139486A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56139486A (en) | 1981-10-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2731853B2 (en) | Method for producing tri-lower alkanoyloxyboron | |
| JPS6247873B2 (en) | ||
| JPH0141152B2 (en) | ||
| JPS6228151B2 (en) | ||
| JP2678758B2 (en) | Novel propane derivative | |
| JPS63162689A (en) | 7-bromo-beta-carboline derivative and production thereof | |
| JPS6043067B2 (en) | 2-Alkoxyindolizine derivatives and their production method | |
| JPH10130244A (en) | Method for producing acyclonucleoside | |
| JPS6043065B2 (en) | Indolizin-2-one derivatives and their production method | |
| JP2659587B2 (en) | 4-aziridinyl pyrimidine derivatives and their production | |
| JPH10168068A (en) | Method for producing acyclonucleoside | |
| JP2706554B2 (en) | 4-trifluoromethylaniline derivative and method for producing the same | |
| JPH08208591A (en) | 2-aminobenzenesulfonic acid derivative and 2-aminobenzenesulfonyl chloride,derivative their production,and their use as synthetic intermediates | |
| JPH0378384B2 (en) | ||
| JPS6344579A (en) | 1-azabicyclononanes and production thereof | |
| US3751462A (en) | Process for preparation of substituted fluoromethanesulfonanilides | |
| JPH0160474B2 (en) | ||
| JP2651658B2 (en) | 1,2,3,5-tetrahydroindolizine derivative | |
| JPS6043066B2 (en) | 2,3-dihydroindolizin-2-one derivative and its production method | |
| JP4055246B2 (en) | 5-chloro-6- (α-fluoroalkyl) -4-pyrimidone and process for producing the same | |
| JPH0217550B2 (en) | ||
| JPS626717B2 (en) | ||
| JPH0662470B2 (en) | Process for producing optically active hexa-2,4-diyne-1,6-diols | |
| JPH0214348B2 (en) | ||
| JPS6159309B2 (en) |