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KMID : 0043319900130040319
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Archives of Pharmacal Research
1990 Volume.13 No. 4 p.319 ~ p.324
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Studies on Synthesis and Heterocyclisation Reactions of Michael Products and Formation of New 1,4-Thiazine Quinoxaline Derivatives
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Mahgoub SA
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Abstract
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Synthesis of alpha-piperidino and alpha-morphelino styryl quinoxalinone 2f,2g respectively by facile one step method is reported. The Michael adducts (3a-d) obtained by the interaction of 2-styryl-2 (1H) quinoxalinone (2) and ethylacetoacetate have been treated with resorcinol and hydroxylamine separatly. With resorcinol the chromones (4) are obtained whereas with hydroxylamine isoxazolones (6) are the products. Michael addition of acetylacetone to 2 leads to 3-[1’’-aryl-2’’-(2’’-hydroxy-3’’-quinoxalinyl)ethyl]-2,4-pentanediones (5) which undergo cyclisation with hydroxylamine to give isoxazoles (7). Addition of thiophenol and thioglycolic acid to 2 gives 3-alpha-[beta-(phenyl)-beta-(plenylthio)]ethyl-2(1H)-quinoxalinone (8) and 3-alpha-[beta-(phenyl)-beta-(hydroxycarbonylmethylthio)]-ethyl-2(1H)-quinoxalinone (9) respectively. 2-Bromomethyl-2(1H)-quinoxalinone (1b) reacts with thioglycolic acid to gives S-[2 (1H)-oxoquinoxalin-3-yl-methyl]mercaptoacetic acid (10) which on cyclisation with acetic anhydride/pyridine affords 1,2,5,6-tetrahydro[1,4]thiazino[4,3-a] quinoxaline-1,6-dione (11).
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