4-(<i>N</i>-BOC-AMINO)-1<i>Н</i>-1,2,3-TRIAZOLECARBOTHIOAMIDES IN THE SYNTHESIS OF A NEW HETEROCYCLIC [1,2,3]TRIAZOLO[4,5-<i>e</i>][1,4]THIAZEPINE SYSTEM

Authors

  • Наталия A. Сирота National University ''Kyiv-Mohyla Academy'', 2 Hryhorija Skovorody St., Kyiv 04655
  • Сергей B. Кемский Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., Kyiv 02660
  • Андрей B. Больбут Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., Kyiv 02660 Enamine Ltd., 78 Chervonotkatska St., Kyiv 02094
  • Игорь И. Чернобаев Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., Kyiv 02660
  • Александр C. Лявинец Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., Kyiv 02660
  • Михаил B. Вовк Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., Kyiv 02660

DOI:

https://doi.org/10.1007/6266

Keywords:

4-(N-Boc-amino)-5-thioimidates, 4-(N-Boc-amino)-1Н-1, 2, 3-triazolecarbothioamides, N-Boc-4-amino-1, 3-triazoles, ethyl bromoacetate, [1, 3]triazolo[1, 4]thiazepines

Abstract

4-(N-Boc-amino)-1Н-1,2,3-triazolecarbothioamides, obtained by a sequential treatment of 4-(N-Boc-amino)-1Н-1,2,3-triazoles with n-BuLi and alkyl isothiocyanates at –78÷–60°C, reacted with ethyl bromoacetate, forming the respective 4-(N-Boc-amino)-5-thioimidates, which underwent intramolecular cyclocondensation upon treatment in saturated НCl solution in dioxane, producing 8-(alkylimino)-4,8-dihydro-1Н-[1,2,3]triazolo[4,5-e][1,4]thiazepin-5(6Н)-ones.

Authors: Natalia A. Syrota, Sergiy V. Kemskiy*, Andriy V. Bol'but, Igor I. Chernobaev, Oleksandr S. Liavinets, Mykhailo V. Vovk

Downloads

Published

2021-08-26

Issue

Vol. 57 No. 7/8 (2021)

Section

Original Papers