Preparation of New Nitrogen-Bridged Heterocycles. XXXI. Cyclization Aptitudes of 2-Acylmethyl-thio-3-cyanoindolizines Having a Cyano or an Ester Group at the 1-Position

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概要

• 論文の詳細を見る

• Some 2-acylmethylthio-3-cyanoindolizine derivatives having a cyano or an ethoxycarbonyl group at the 1-position were prepared and their intramolecular cyclization reactions were examined. The alkaline treatment of these polyfunctionalized indolizines in refluxing ethanol gave only 3-aminothieno[2,3-b]indolizine derivatives in moderate to good yields regardless of the kind of 1-substituent, and the other possible alternative, a thieno[3,2-α]indolizine derivative, could not be obtained at all. The higher reactivity of the 3-cyano group over 1-cyano and 1-ethoxycarbonyl groups coincided well with the results expected from molecular orbital calculations for the model compounds. From our present and previous results, the order (3-CN>1-CN>3-ester>1-ester) of the reactivities of electron-withdrawing groups at the 1- and 3-positions on the indolizing ring was finally estblished.

• 社団法人日本薬学会の論文
• 1992-09-25

著者

• 筧 昭一

  Department Of Chemistry And Material Engineering Faculty Of Engineering Shinshu University

• 伊東 祐隆

  Department of Chemistry and Material Engineering, Faculty of Engineering, Shinshu University

• 上田 達也

  Department of Chemistry and Material Engineering, Faculty of Engineering, Shinshu University

• 藤井 恒男

  Department of Chemistry and Material Engineering, Faculty of Engineering, Shinshu University

• 平田 智裕

  Department of Chemistry and Material Engineering, Faculty of Engineering, Shinshu University

• 平田 智裕

  Department Of Chemistry And Material Engineering Faculty Of Engineering Shinshu University

• 伊東 祐隆

  Department Of Chemistry And Material Engineering Faculty Of Engineering Shinshu University

• 藤井 恒男

  Department Of Chemistry And Material Engineering Faculty Of Engineering Shinshu University

• 上田 達也

  Department Of Chemistry And Material Engineering Faculty Of Engineering Shinshu University

関連論文

• Preparation of New Nitrogen-Bridged Heterocycles. XXXIII. A New Preparative Method for Thieno[3,2-α]indolizines
• Preparation of New Nitrogen-Bridged Heterocycles. XXXI. Cyclization Aptitudes of 2-Acylmethyl-thio-3-cyanoindolizines Having a Cyano or an Ester Group at the 1-Position
• Preparation of New Nitrogen-Bridged Heterocycles. XXVI. Crystal Structures of Thieno[3,2-a]-and Thieno[2,3-b]indolizine Derivatives
• Preparation of New Nitrogen-Bridged Heterocycles. XXIV. : Syntheses and Reactions of Pyrazolo[1,5-a]pyridine-2-thiols. (2)
• Preparation of New Nitrogen-Bridged Heterocycles. XXIII. : Syntheses and Reactions of Pyrazolo[1,5-a]pyridine-2-thiols. (1)
• Preparation of New Nitrogen-Bridged Heterocycles. XXII. : A New Approach to the Syntheses of Thienoindolizine Derivatives
• Preparation of New Nitrogen-Bridged Heterocycles. XIV. Further Investigation of the Desulfurization and the Rearrangement of Pyrido[1,2-d]-1,3,4-thiadiazine Intermediates(Organic,Chemical)
• Preparation of New Nitrogen-Bridged Heterocycles. XIII. : Syntheses of Some Tricyclic and Tetracyclic Indolizine Derivatives with Antiallergic Activity

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