Regioselective synthesis of tetrasubstituted pyrroles by 1,3-dipolar cycloaddition and spontaneous decarboxylation.
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).
Kim
Yongju
Y
Department of Chemistry, Seoul National University, Seoul 151-747, Korea.
Kim
Jonghoon
J
Park
Seung Bum
SB
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
D001572:Benzofurans; D007783:Lactones; D011758:Pyrroles