title: Regioselective synthesis of tetrasubstituted pyrroles by 1,3-dipolar cycloaddition and spontaneous decarboxylation.
abstract: We developed a novel regioselective synthesis of tetrasubstituted pyrroles via the classic 1,3-dipolar cycloaddition of alpha,beta-unsaturated benzofuran-3(2H)-one and azlactones (1) followed by spontaneous decarboxylation. The complete regiochemical control of tetrasubstituted pyrroles was confirmed by the orthogonal synthesis of complementary regioisomers (7a and 7b) simply by using different azlactones (1a and 1b, respectively).
authors.affiliation: Department of Chemistry, Seoul National University, Seoul 151-747, Korea.
authors.forename: Yongju
authors.initials: Y
authors.lastname: Kim
authors.forename: Jonghoon
authors.initials: J
authors.lastname: Kim
authors.forename: Seung Bum
authors.initials: SB
authors.lastname: Park
mesh_terms: D001572:Benzofurans / Q000737:chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D003653:Decarboxylation; D007783:Lactones / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001572:Benzofurans; D007783:Lactones; D011758:Pyrroles