Synthesis of Condensed Quinoxalines. VI. Synthesis of 1H-Pyrazolo [3,4-b] quinoxaline N-Oxides and Related Compounds

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概要

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• Oxidation of 1H-pyrazolo [3,4-b] quinoxalines (1a : R=H, 1b : R=CH_3) with m-chloroperbenzoic acid (MCPBA) gave the 4-oxides (2a, b). The structures of 2a, b were confirmed by synthesis, by condensing 2-chloroquinoxaline-3-carbaldehyde 4-oxide (6) with appropriate hydrazines. Further oxidation of 2a with MCPBA gave the 4,9-dioxide (8). Treatment of 1,2-dihydro-2-oxoquinoxaline-3-carboxamide (10) and 1,2-dihydro-2-oxoquinoxaline-3-carbonitrile 4-oxide (13) with a mixture of POCl_3 and PCl_5 or POCl_3-dimethyl-formamide afforded 2-chloroquinoxaline-3-carbonitrile (11) and its 4-oxide (14), respectively. When 11 and 14 were reacted with hydrazines, the corresponding 3-amino-1H-pyrazolo [3,4-b]-quinoxalines (12a, b) and their 4-oxides (15a, b) were obtained in high yields. The reaction of ethyl 2-chloroquinoxaline-3-carboxylate (16) with hydrazine hydrate afforded a mixture of uncyclized products, N, N'-bis (2-ethoxycarbonyl-3-quinoxalinyl) hydrazine (17), ethyl 2-hydrazinoquinoxaline-3-carboxylate (18) and 2-hydrazinoquinoxaline-3-carbohydrazide (19).

• 社団法人日本薬学会の論文
• 1984-09-25

著者

• 乙益 寛隆

  Faculty of Pharmaceutical Sciences, Hoshi University

• 乙益 寛隆

  Faculty Of Pharmaceutical Sciences Hoshi University

• 吉田 桂

  Faculty of Pharmaceutical Sciences, Hoshi University

• 吉田 桂

  Faculty Of Pharmaceutical Sciences Hoshi University

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