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Davis-Beirut reaction: route to thiazolo-, thiazino-, and thiazepino-2H-indazoles.

  • Author(s): Farber, Kelli M
  • Haddadin, Makhluf J
  • Kurth, Mark J
  • et al.

Published Web Location

https://doi.org/10.1021/jo501014e
Abstract

Methods for the construction of thiazolo-, thiazino-, and thiazepino-2H-indazoles from o-nitrobenzaldehydes or o-nitrobenzyl bromides and S-trityl-protected 1°-aminothioalkanes are reported. The process consists of formation of the requisite N-(2-nitrobenzyl)(tritylthio)alkylamine, subsequent deprotection of the trityl moiety with TFA, and immediate treatment with aq. KOH in methanol under Davis-Beirut reaction conditions to deliver the target thiazolo-, thiazino-, or thiazepino-2H-indazole in good overall yield. Subsequent S-oxidation gives the corresponding sulfone.

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