title: Synthesis of substituted 2-aminoimidazoles via Pd-catalyzed alkyne carboamination reactions. Application to the synthesis of preclathridine natural products.
abstract: A new method for the synthesis of 2-aminoimidazole products is described. The heterocyclic products are generated in good yields via Pd-catalyzed carboamination reactions of N-propargyl guanidines and aryl triflates. This methodology generates both a C-N and C-C bond during the annulation step and facilitates the rapid construction of 2-aminoimidazole products with different aryl groups. The utility of this methodology was demonstrated in the total synthesis of preclathridine A, preclathridine B, and dorimidazole B from a single intermediate.
authors.affiliation: Department of Chemistry, University of Michigan , 930 North University Avenue, Ann Arbor, Michigan 48109-1005, United States.
authors.forename: Blane P
authors.initials: BP
authors.lastname: Zavesky
authors.forename: Nicholas R
authors.initials: NR
authors.lastname: Babij
authors.forename: John P
authors.initials: JP
authors.lastname: Wolfe
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D006146:Guanidines / Q000737:chemistry; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*
chemical_list: D000470:Alkaloids; D001688:Biological Products; D006146:Guanidines; D007093:Imidazoles; C551550:clathridine; C000599339:dorimidazole B; C000599337:preclathridine A; C000599338:preclathridine B; D010165:Palladium; C014973:2-aminoimidazole