A new synthesis of bicyclic N,O- and N,S-enaminals by the anionic cyclization of alk-4-ynals with amino alcohols and amino thiols |
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Authors: | V D Gvozdev K N Shavrin O M Nefedov |
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Institution: | 1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation
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Abstract: | A reaction of alk-4-ynals with aliphatic amino alcohols or 2-aminoethanethiol in the system DMSO—KOH gives bicyclic N,O- and N,S-enaminals: 6-methylidenehexahydro-2H-pyrrolo2,1-b]1,3]oxazines, 5-methylidenehexahydropyrrolo2,1-b]oxazoles, or 5-methyl-idenehexahydropyrrolo2,1-b]thiazoles. The reaction proceeds through the formation of equilibrium mixtures of the corresponding imines and monocyclic aminals with subsequent 5-exodig-cyclization catalyzed by the superbasic system DMSO-KOH. |
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