Transannular anti-Michael addition: formation of 4H-pyrazolo[5,1-c]thiazines

Yat Fan Suen, Håkon Hope, Michael H. Nantz, Makhluf J. Haddadin, Mark J. Kurth

Research output: Contribution to journalArticle

9 Scopus citations

Abstract

The reaction of 2-(diphenylmethylene)thietan-3-one (2) with 1,2,4,5-tetrazines (3a-c) in KOH/MeOH/THF gives 4H-pyrazolo[5,1-c]thiazines (7a-c). This novel condensation reaction proceeds via the intermediacy of an 8-(diphenylmethylene)-2H-1,4,5-thiadiazocin-7(8H)-one (5), which undergoes a multi-step rearrangement including a rare anti-Michael addition.

Original languageEnglish (US)
Pages (from-to)7893-7896
Number of pages4
JournalTetrahedron Letters
Volume47
Issue number45
DOIs
StatePublished - Nov 6 2006

Keywords

  • 4H-Pyrazolo[5,1-c]thiazine
  • Anti-Michael addition
  • Pyrazole

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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    Suen, Y. F., Hope, H., Nantz, M. H., Haddadin, M. J., & Kurth, M. J. (2006). Transannular anti-Michael addition: formation of 4H-pyrazolo[5,1-c]thiazines. Tetrahedron Letters, 47(45), 7893-7896. https://doi.org/10.1016/j.tetlet.2006.09.015