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4-(N-Boc-amino)-1Н-1,2,3-triazolecarbothioamides in the synthesis of a new heterocyclic [1,2,3]triazolo[4,5-e][1,4]thiazepine system

Chem. Heterocycl. Compd. 2021, 57 (7-8), 841-847

DOI: 10.1007/s10593-021-02989-1

Syrota N.; Kemskiy S.; Bol’but A.; Chernobaev I.; Liavinets O.; Vovk M.

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.

4-(N-Boc-amino)-1Н-1,2,3-triazolecarbothioamides in the synthesis of a new heterocyclic [1,2,3]triazolo[4,5-e][1,4]thiazepine system

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