Domino Michael addition-carbene rearrangement-cyclization reaction of 1-alkynyl(aryl)-lambda3-bromanes with 2-mercapto-1,3-benzazoles.
Exposure of 1-alkynyl[p-(trifluoromethyl)phenyl](tetrafluoroborato)-lambda3-bromanes to 2-mercaptobenzimidazole or benzothiazole in dichloromethane at 0 degrees C under argon resulted in a domino Michael addition-carbene rearrangement-cyclization reaction to produce directly tricyclic heterocycles in high yields, whereas the reaction with 2-mercaptobenzoxazole afforded 1-alkynyl sulfides.
Ochiai
Masahito
M
Faculty of Pharmaceutical Sciences, University of Tokushima, 1-78 Shomachi, Tokushima 770-8505, Japan. mochiai@ph.tokushima-u.ac.jp
Tada
Norihiro
N
D000478:Alkylation; D001554:Benzene / Q000737:chemistry*; D052160:Benzothiazoles / Q000737:chemistry; D017605:Bromine Compounds / Q000737:chemistry*; D003500:Cyclization; D005449:Fluorenes / Q000737:chemistry; D006838:Hydrocarbons / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D013438:Sulfhydryl Compounds / Q000737:chemistry*
D052160:Benzothiazoles; D017605:Bromine Compounds; D005449:Fluorenes; D006838:Hydrocarbons; D013438:Sulfhydryl Compounds; C030011:carbene; C041509:fluorene; C005465:benzothiazole; D001554:Benzene; D008697:Methane