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Phosphorylthioacetamides in the synthesis of annulated quinoxalines
Authors:D V Aleksanyan  V A Kozlov  I L Odinets  P V Petrovskii  T A Mastryukova
Institution:(1) A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991 Moscow, Russian Federation
Abstract:Diethoxyphosphorylthioacetamide in the reaction with 2,3-dichloroquinoxaline acted as a thionating reagent, giving diethoxyphosphorylacetonitrile and 2-chloro-3-(3-chloro-2-quinoxalinyl)thio]quinoxaline. Reactions of phosphorylthioacetamides with N-methylquinoxalinium iodide in alcohol media in the presence of a base proceeded stereoselectively to afford cis-3-phosphoryl-1,3,3a,4,9,9a-hexahydro-2H-pyrrolo2,3-b]quinoxaline-2-thiones. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 1010–1013, May, 2007.
Keywords:phosphorylthioacetamides  2  3-dichloroquinoxaline            N-methylquinoxalinium iodide  annulation  1  3  3a  4  9  9a-hexahydro-2H-pyrrolo[2  3-b]quinoxaline-2-thiones
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