TRANSFORMATIONS OF TETRAHYDRO-1,4-BENZOXAZEPINES AND TETRAHYDRO-1,4-BENZOTHIAZEPINES UNDER THE ACTION OF ALKYNES. FIRST EXAMPLE OF THE SYNTHESIS OF TETRAHYDRO-1,4-BENZOTHIAZONINE-6-CARBOXYLATE

Authors

  • Л. Г. Воскресенский Peoples' Friendship University of Russia
  • С. В. Акбулатов Peoples' Friendship University of Russia
  • Т. Н. Борисова Peoples' Friendship University of Russia
  • Л. Н. Куликова Peoples' Friendship University of Russia
  • А. В. Листратова Peoples' Friendship University of Russia
  • Е. А. Сорокина Peoples' Friendship University of Russia
  • А. В. Варламов Peoples' Friendship University of Russia

DOI:

https://doi.org/10.1007/415

Keywords:

alkynes, benzoxazepine, benzothiazepine, benzothiazonine, domino reaction, ring expansion, ring cleavage

Abstract

It was shown that 2,3,4,5-tetrahydro-1,4-benzoxazepines were cleaved at the N-C(5) bond under the action of activated alkynes in methanol, forming o-(methoxyethyl)- and o-(methoxybenzyl)-phenyl(aminoethyl) ethers. The cleavage rate depended on the electronic effects of the substituents at the C-5 atom. Thiazepine ring expansion in tetrahydro-1,4-benzothiazepine was achieved for the first time via reaction with methyl propiolate to give a benzothiazonine.

Authors: L. G. Voskressensky, S. V. Akbulatov, T. N. Borisova, L. N. Kulikova, A. V. Listratova, E. A. Sorokina, and A. V. Varlamov

English Translation in Chemistry of Heterocyclic Compounds, 2013, 49 (2), pp 331-340

http://link.springer.com/article/10.1007/s10593-013-1251-z

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Published

2013-03-19

Issue

No. 2 (2013)

Section

Original Papers