Nucleophilic capture of the imino-quinone methide type intermediates generated from 2-aminothiazol-5-yl carbinols.
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.
Saulnier
Mark G
MG
Department of Discovery Chemistry, Bristol-Myers Squibb Pharmaceutical Research Institute, 5 Research Parkway, Wallingford, Connecticut 06492, USA. mark.saulnier@bms.com
Dodier
Marco
M
Frennesson
David B
DB
Langley
David R
DR
Vyas
Dolatrai M
DM
D007097:Imines / Q000737:chemistry*; D045563:Indolequinones / Q000138:chemical synthesis* / Q000737:chemistry; D000432:Methanol / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013844:Thiazoles / Q000737:chemistry*
C546265:2-aminothiazol-5-yl carbinol; D007097:Imines; D045563:Indolequinones; D013844:Thiazoles; C068040:quinone methide; D000432:Methanol