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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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Abstract

Synthesis of α-piperidino and α-morphelino styryl’quinoxalinone2f, 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 to2 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 to2 gives3-α-[β-(phenyl)-β-(plenylthio)]ethyl-2(1H)-quinoxalinone (8) and 3-α-[β-phenyl)-β-(hydroxycarbonylmethylthio)]-ethyl-2(1H)-quinox-alinone (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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  1. Chemistry Department, Faculty of Science, Assiut University, Assiut, Egypt

    S. A. Mahgoub

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Mahgoub, S.A. Studies on synthesis and heterocyclisation reactions of michael products and formation of new 1,4-thiazine quinoxaline derivatives. Arch. Pharm. Res. 13, 319–324 (1990). https://doi.org/10.1007/BF02858166

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  • DOI: https://doi.org/10.1007/BF02858166

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