Preparation of New Nitrogen-Bridged Heterocycles. XXIV. : Syntheses and Reactions of Pyrazolo[1,5-a]pyridine-2-thiols. (2)

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概要

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• Various 2-(acylmethylthio)-, 2-(benzylthio)-, and 2-(propargylthio)pyrazolo[1,5-a]pyridine derivatives (4a-n' and 7a-n') were prepared in moderate to good yields by the reactions of potassium pyrazolo[1,5-a]pyridine-2-thiolates (2 and 6), readily available by the treatment of 2-[(2-ethoxycarbonylethyl)thio]- and 2-[(2-cyanoethyl)thio]pyrazolo[1,5-a]pyridines (1a-h and 5a-h) with potassium tert-butoxide in N, N-dimethylformamide (DMF), with alkylating agents such as chloroacetone (3a), phenacyl bromides (3b-d), ethyl bromoacetate (3e), benzyl bromides (3f-k), and propargyl bromide (31). Of these S-functionalied pyrazolo[1,5-a]pyridines only 2-(acetonylthio)- and 2-(phenacylthio)pyrazolo[1,5-a]pyridine-3-carbonitriles (4a-t) were converted to new heterocyles, thieno[2', 3' : 3,4]pyrazolo[1,5-a]pyridines (8a-t) by heating them with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU); the other compounds did not provide any tricyclic heterocycles under various alkaline conditions. The structures of thieno[2', 3' : 3,4]pyrazolo[1,5-a]pyridines (8a-t) were determined mainly by elemental analyses and spectral inspections, and the structural assignment was confirmed by the X-ray analysis of compound 8d.

• 社団法人日本薬学会の論文
• 1990-10-25

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

• 櫻井 敏雄

  Department of Chemistry, Faculty of Education, Shinshu University

• 漆戸 邦夫

  Department of Chemistry, Faculty of Education, Shinshu University

• 伊沢 英俊

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

• 高嶋 庸晃

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

• 櫻井 敏雄

  Department Of Chemistry Faculty Of Education Shinshu University

• 漆戸 邦夫

  Department Of Chemistry Faculty Of Education Shinshu University

• 高嶋 庸晃

  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

• 伊沢 英俊

  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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