AN UNEXPECTED SYNTHESIS OF β-AMINO-α-MESYL-γ-SULTAMS UPON MESYLATION OF HINDERED α-AMINONITRILES

Authors

  • Maksim S. Dyachenko Enamine Ltd., 78 Chervonotkatska St., Kyiv 02094 Enamine Ltd., Kyiv, Ukraine Taras Shevchenko National University of Kyiv, 60 Volodymyrska St., Kyiv 01601
  • Alexey V. Dobrydnev Enamine Ltd., 78 Chervonotkatska St., Kyiv 02094 Enamine Ltd., Kyiv, Ukraine Taras Shevchenko National University of Kyiv, 60 Volodymyrska St., Kyiv 01601
  • Yaroslav O. Chuchvera Enamine Ltd., 78 Chervonotkatska St., Kyiv 02094 Enamine Ltd., Kyiv, Ukraine Taras Shevchenko National University of Kyiv, 60 Volodymyrska St., Kyiv 01601
  • Svitlana V. Shishkina State Scientific Institution ''Institute for Single Crystals'', National Academy of Science of Ukraine, 60 Nauky Ave., Kharkiv 61001 Department of Inorganic Chemistry, V. N. Karazin Kharkiv National University, 4 Svobody Sq., Kharkiv 61077
  • Yulian M. Volovenko Taras Shevchenko National University of Kyiv, 60 Volodymyrska St., Kyiv 01601

DOI:

https://doi.org/10.1007/5476

Keywords:

aminonitriles, spiro compounds, sulfonamides, cyclization, X-ray study

Abstract

We report one-pot procedure for an unexpected synthesis of previously unknown 4-amino-5-methylsulfonyl-2,3-dihydroisothiazole 1,1-dioxides (also called β-amino-α-mesyl-γ-sultams). Thus, the reaction of mesyl chloride with hindered α-aminonitriles is accompanied by the formation of interim N-(1-cyanoalkyl)(methylsulfonyl)methanesulfonamides which, in turn, undergo the сarbanion-mediated sulfonate (sulfonamido) intramolecular cyclization reaction yielding β-amino-α-mesyl-γ-sultams. The structure of the title compounds was confirmed by X-ray diffraction study. The proposed mechanistic insights of the reaction are in accordance with the results of additional experiments and literature data.

Author Biography

Alexey V. Dobrydnev, Enamine Ltd., 78 Chervonotkatska St., Kyiv 02094 Enamine Ltd., Kyiv, Ukraine Taras Shevchenko National University of Kyiv, 60 Volodymyrska St., Kyiv 01601

Faculty of Chemistry, Department of Organic Chemistry

Researcher

Published

2020-04-01

Issue

Section

Original Papers