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Interaction of Methyl N-(3-oxoalkyl)carbamates, S-methyl -Carbamates, and -Dithiocarbamates with Sodium Borohydride. Synthesis of Tetrahydro-1,3-oxazin-2-ones and -thiones

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Abstract

The interaction of N-(3-oxoalkyl)carbamates, -thiocarbamates, and -dithiocarbamates with sodium borohydride has been studied. It was shown that reaction proceeds diastereoselectively, and reductive cyclization with the formation of tetrahydro-1,3-oxazin-2-ones and -thiones may occur. The tend to cyclization of the N-(3-hydroxyalkyl)carbamates, -thiocarbamates, and -dithiocarbamates formed as intermediates depends on the number of substituents in the alkyl chain.

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Authors and Affiliations

  1. Omsk State University, Omsk, 644077, Russia

    A. S. Fisyuk, E. A Ryzhova & B. V. Unkovskii

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  1. A. S. Fisyuk
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  2. E. A Ryzhova
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  3. B. V. Unkovskii
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Fisyuk, A.S., Ryzhova, E.A. & Unkovskii, B.V. Interaction of Methyl N-(3-oxoalkyl)carbamates, S-methyl -Carbamates, and -Dithiocarbamates with Sodium Borohydride. Synthesis of Tetrahydro-1,3-oxazin-2-ones and -thiones. Chemistry of Heterocyclic Compounds 37, 597–609 (2001). https://doi.org/10.1023/A:1011660706513

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