Davis-Beirut reaction: Route to thiazolo-, thiazino-, and thiazepino-2 h -indazoles

Kelli M. Farber, Makhluf J. Haddadin, Mark J. Kurth

Research output: Contribution to journalArticle

11 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)6939-6945
Number of pages7
JournalJournal of Organic Chemistry
Volume79
Issue number15
DOIs
StatePublished - 2014

ASJC Scopus subject areas

  • Organic Chemistry
  • Medicine(all)

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