Nucleophilic capture of the imino-quinone methide type intermediates generated from 2-aminothiazol-5-yl carbinols

Mark G Saulnier; Marco Dodier; David B Frennesson; David R Langley; Dolatrai M Vyas

doi:10.1021/ol902023g

Nucleophilic capture of the imino-quinone methide type intermediates generated from 2-aminothiazol-5-yl carbinols

Org Lett. 2009 Nov 19;11(22):5154-7. doi: 10.1021/ol902023g.

Authors

Mark G Saulnier¹, Marco Dodier, David B Frennesson, David R Langley, Dolatrai M Vyas

Affiliation

¹ Department of Discovery Chemistry, Bristol-Myers Squibb Pharmaceutical Research Institute, 5 Research Parkway, Wallingford, Connecticut 06492, USA. [email protected]

PMID: 19827772
DOI: 10.1021/ol902023g

Abstract

Generation of imino-quinone methide type intermediates from 2-aminothiazole-5-carbinols using alkylsulfonic acids in nitromethane followed by trapping with a wide range of nucleophiles effects C-C, C-O, C-N, C-S, and C-P bond formation.

MeSH terms

Imines / chemistry*
Indolequinones / chemical synthesis*
Indolequinones / chemistry
Methanol / analogs & derivatives*
Methanol / chemistry
Molecular Structure
Stereoisomerism
Thiazoles / chemistry*

Substances

2-aminothiazol-5-yl carbinol
Imines
Indolequinones
Thiazoles
quinone methide
Methanol