Synthesis of 1,3-Oxazino [5,6-c] isoquinolines and Related Compounds

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概要

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• Mannich reaction of 1-chloro-4-isoquinolinol (1) with dimethylamine and formalin afforded the base, 1-chloro-3-dimethylaminomethyl-4-isoquinolinol (2), and a by-product, 1,1'-dichloro-3,3'-methylenedi-4-isoquinolinol (3). The reaction of 1 with formalin in H_2SO_4 gave 6-chloro-1,3-dioxino [5,6-c] isoquinoline (4). The reactions of 1 with formalin and primary amines, and of 1 with acetaldehyde ammonia afforded the corresponding products, 1,3-oxazino [5,6-c] isoquinolines (5-7), in fair yields. Methyl 4-hydroxy-1-oxo-1,2-dihydroisoquinoline-3-carboxylate (8) was converted into the carboxamide (9), which, on heating with a mixture of POCl_3 and PCl_5,afforded two chloro-cyano compounds 10 and 11 in a ratio of ca. 1 : 2. The reaction of 11 with hydrazine hydrate gave the 1-hydrazino compound (13).

• 社団法人日本薬学会の論文
• 1985-12-25

著者

• 乙益 寛隆

  Hoshi College of Pharmacy

• 乙益 寛隆

  Faculty of Pharmaceutical Sciences, Hoshi University

• 乙益 寛隆

  Faculty Of Pharmaceutical Sciences Hoshi University

• 外山 美代子

  Department of Pharmacy, College of Science and Technology, Nihon University

• 外山 美代子

  Department Of Pharmacy College Of Science And Technology Nihon University

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