Reaction of quinones and guanidine derivatives: simple access to bis-2-aminobenzimidazole moiety of benzosceptrin and other benzazole motifs.
A new strategy for the synthesis of 2-aminobenzimidazol-6-ols via a reaction of quinones with guanidine derivatives is reported. Sequential application of this methodology provided a simple access to the first benzosceptrin analogue bearing a bis-2-aminoimidazole moiety. A concomitant addition of two guanidines to the naphtho[1',2':4,5]imidazo[1,2-a]pyrimidine-5,6-dione, which includes the redox neutral debenzylation and guanidine-assisted cleavage of the 2-aminopyrimidine part resulted in the synthesis of the free challenging contiguous bis-2-aminoimidazole moiety of benzosceprins in one step.
Centre de Recherche de Gif-sur-Yvette, Institut de Chimie des Substances Naturelles , CNRS, 91198 Gif-sur-Yvette Cedex, France .
Minh Quan
MQ
Tran
Ludmila
L
Ermolenko
Pascal
P
Retailleau
Thanh Binh
TB
Nguyen
Ali
A
Al-Mourabit
D001562:Benzimidazoles / Q000138:chemical synthesis* / Q000737:chemistry*; D006146:Guanidines / Q000737:chemistry*; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry*; D011809:Quinones / Q000737:chemistry*
D001562:Benzimidazoles; D006146:Guanidines; D007093:Imidazoles; D009281:Naphthalenes; D011758:Pyrroles; D011809:Quinones; C545619:benzosceptrin A; C014973:2-aminoimidazole; C027391:2-aminobenzimidazole