Preparation of New Nitrogen-Bridged Heterocycles. XXII. : A New Approach to the Syntheses of Thienoindolizine Derivatives

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概要

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• Ethyl 2-[(2-substituted ethyl)thio]-3-indolizinecarboxylates (1a-f and 5a-f) were deprotected with potassium tert-butoxide in N, N-dimethylformamide and the resulting potassium 2-indolizinethiolates were alkylated with various alkylating agents such as chloroacetone (3a), phenacyl bromides (3b-d), and nitrobenzyl bromides (3e, f) to afford smoothly the corresponding S-functinoalized indolizine derivatives (4a-r and 6a-r) in considerable yields. On the other hand, the similar reactions of 3-acetyl-2-[(2-substituted ethyl)thio]indolizines (7a-f) provided 3-metylthieno[2,3-b]indolizine derivatives (8a-o), formed via the further intramolecular cyclization of the initially generated S-alkylated indolizines under the reaction conditions employed here. The functionalized indolizines (4a-r and 6a-r) obtained above could also be transformed to the corresponding thieno[3,2-α]-(10a-r, 14a-d, and 15a, b) and thieno[2,3-b]indolizine derivatives (11a-h and 12a-d) under various alkaline conditions.

• 社団法人日本薬学会の論文
• 1990-06-25

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

• 山田 直明

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

• 山口 公伸

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

• 山口 公伸

  Department Of Chemistry And Material Engineering Faculty Of Engineering Shinshu University

• 山田 直明

  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

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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