The N-Oxides of New Heterocyclic Systems. Syntheses and Chemical Properties of Thiazolo [4,5-g] quinazoline 3-Oxides and Thiazolo [5,4-f] quinazoline 3-Oxides

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概要

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• Thiazolo [4,5-g] quinazoline 3-oxides and thiazolo [5,4-f] quinazoline 3-oxides, the N-oxides of new heterocyclic systems, were synthesized and their chemical properties were investigated. Namely, the reaction of 7-chloro-1,3-dimethyl-6-nitroquinazoline-2,4 (1H, 3H)-dione (1) with methyl thioglycolate in the presence of triethylamine gave 7-methoxycarbonylmethylthio-1,3-dimethyl-6-nitroquinazoline-2,4 (1H, 3H)-dione (2) and subsequent treatment of 2 with pyrrolidine resulted in base-catalyzed dehydrative cyclization to afford 2-methoxycarbonyl-6,8-dimethylthiazolo [4,5-g] quinazoline-5,7 (6H, 8H)-dione 3-oxide (3) and 6,8-dimethyl-2-pyrrolidinocarbonylthiazolo [4,5-g] quinazoline-5,7-(6H, 8H)-dione 3-oxide (5). On the other hand, the reaction of 5-chloro-1,3-dimethyl-6-nitroquinazoline-2,4 (1H, 3H)-dione (10) with methyl thioglycolate in the presence of triethylamine directly yielded 2-methoxycarbonyl-6,8-dimethylthiazolo [5,4-f] quinazoline-7,9 (6H, 8H)-dione 3-oxide (11). These N-oxides were confirmed to be useful starting materials for the preparation of a variety of thiazolo [4,5-g]- and [5,4-f] quinazoline derivatives.

• 公益社団法人日本薬学会の論文
• 1985-02-25

著者

• 金沢 一

  Pharmaceutical Institute, School of Medicine, Keio, University

• 田村 善蔵

  Pharmaceutical Institute, School of Medicine, Keio, University

• 千賀 慶太郎

  Pharmaceutical Institute, School of Medicine, Keio, University

• 千賀 慶太郎

  Pharmaceutical Institute School Of Medicine Keio University

• 千賀 慶太郎

  慶応大 病院

• 千賀 慶太郎

  慶応義塾大学病院薬剤部

• 金沢 一

  慶應義塾大学病院薬剤部

• 田村 善蔵

  Pharmaceutical Institute School Of Medicine Keio University

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