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Trisubstituted 1,3,5-Triazines. 5. Reaction of 2,4,6-Tris[di(tert-butoxycarbonyl)nitromethyl]-1,3,5-triazine with Nucleophiles

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The reaction of 2,4,6-tris[di(tert-butoxycarbonyl)nitromethyl]-1,3,5-triazine with ammonia, amines, and hydrazine has been studied. It was possible to substitute one of the di(tert-butoxycarbonyl)nitromethyl groups in this compound in the presence of ammonia, primary aliphatic amines, dimethylamine, and morpholine. The reaction with hydrazine leads to both mono- and disubstituted products. A double dealkoxylation occurs in the presence of diethylamine to give the bis(dimethylammonium) salt of 2,4-bis(tert-butoxycarbonylnitromethyl)-6-[di(tert-butoxycarbonyl)nitromethyl]-1,3,5-triazine.

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Authors and Affiliations

  1. Russian Academy of Sciences, Institute for Problems in Chemical Physics, Chernogolovka, 142432, Russia

    A. V. Shastin

  2. N. D. Zelinsky Institute of Organic Chemistry, Moscow, 117913, Russia

    T. I. Godovikova & B. L. Korsunskii

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  1. A. V. Shastin
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  2. T. I. Godovikova
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  3. B. L. Korsunskii
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Shastin, A.V., Godovikova, T.I. & Korsunskii, B.L. Trisubstituted 1,3,5-Triazines. 5. Reaction of 2,4,6-Tris[di(tert-butoxycarbonyl)nitromethyl]-1,3,5-triazine with Nucleophiles. Chemistry of Heterocyclic Compounds 39, 624–631 (2003). https://doi.org/10.1023/A:1025150216863

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