Access to N-thioalkenyl and N-(o-thio)aryl-benzimidazol-2-ones by ring opening of thiazolobenzimidazolium and benzimidazobenzothiazolium salts and C-O bond cleavage of an alkoxide.
We report herein the synthesis of highly functionalized 1,3-dihydro-2H-benzimidazol-2-ones via a ring opening of thiazolo[3,2-a]benzimidazolium or benzimidazo[2,1-b][1,3]benzothiazol-6-ium salts and an unusual C-O bond cleavage of an alkoxide. A large variety of benzimidazolones bearing an original N-thioalkenyl or N-(o-thio)aryl group was obtained in high yields. The developed chemistry provides efficient and rapid access to the privileged benzimidazol-2-one scaffold.
†Aix Marseille Université, Centrale Marseille, CNRS, iSm2 UMR 7313, 13397 Marseille, France.
Federico
F
Andreoli
‡Laboratoire de synthèse organique appliquée, Département de Chimie, Faculté des Sciences, Université d'Oran (Es Sénia), B.P. 1524, El M'naouer Oran, Algérie.
Radia
R
Kaid-Slimane
†Aix Marseille Université, Centrale Marseille, CNRS, iSm2 UMR 7313, 13397 Marseille, France.
Fabien
F
Coppola
†Aix Marseille Université, Centrale Marseille, CNRS, iSm2 UMR 7313, 13397 Marseille, France.
Daniel
D
Farran
†Aix Marseille Université, Centrale Marseille, CNRS, iSm2 UMR 7313, 13397 Marseille, France.
Christian
C
Roussel
†Aix Marseille Université, Centrale Marseille, CNRS, iSm2 UMR 7313, 13397 Marseille, France.
Nicolas
N
Vanthuyne
D001562:Benzimidazoles / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D010087:Oxides / Q000737:chemistry*; D012492:Salts / Q000737:chemistry; D013844:Thiazoles / Q000737:chemistry*
D001562:Benzimidazoles; D010087:Oxides; D012492:Salts; D013844:Thiazoles; C073244:1-(2',6'-difluorophenyl)-1H,3H-thiazolo(3,4-a)benzimidazole; C053110:benzimidazol-2-one