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

10 Citations (Scopus)

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

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Indazoles
2-nitrobenzaldehyde
Sulfones
Bromides
Methanol
Oxidation

ASJC Scopus subject areas

  • Organic Chemistry
  • Medicine(all)

Cite this

Davis-Beirut reaction : Route to thiazolo-, thiazino-, and thiazepino-2 h -indazoles. / Farber, Kelli M.; Haddadin, Makhluf J.; Kurth, Mark J.

In: Journal of Organic Chemistry, Vol. 79, No. 15, 2014, p. 6939-6945.

Research output: Contribution to journalArticle

Farber, Kelli M. ; Haddadin, Makhluf J. ; Kurth, Mark J. / Davis-Beirut reaction : Route to thiazolo-, thiazino-, and thiazepino-2 h -indazoles. In: Journal of Organic Chemistry. 2014 ; Vol. 79, No. 15. pp. 6939-6945.
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