Synthesis of Heteroaryl-Substituted Pyrroles via the 1,3-Dipolar Cycloaddition of Unsymmetrical Münchnones and Nitrovinylheterocycles

Abstract

A series of furanyl-, thiophenyl-, and pyrrolo-substituted pyrroles were prepared via the 1,3-dipolar cycloaddition of unsymmetrical münchnones and nitrovinylheterocycles. The regiochemical outcome of the furan and thiophene cycloadditions compares favorably to previously reported cycloadditions with β-nitrostyrene, while the nitrovinylpyrrole cycloadditions mirror the results observed with nitrovinylindole.

Functionalized 2,3′-Bipyrroles and Pyrrolo[1,2-c]imidazoles from Acylethynylpyrroles and Tosylmethylisocyanide

“… Synthetic approaches toward 2,3′-bipyrroles. ( a ) 1,3-Dipolar cycloaddition of unsymmetrical münchnones and nitrovinylheterocycles [ 17 ]; ( b ) Cycloaddition of acylethynylpyrroles with diethyl aminomalonate hydrochloride [ 18 ]. Previous works.…”

“…Only a few preparative significant methods for the synthesis of these assemblies are known. Among them are 1,3-dipolar cycloaddition of unsymmetrical münchnones and nitrovinylheterocycles in the presence of N,N ′-diisopropylcarbodiimide (DIPC) ( Scheme 1 a) [ 17 ] and cycloaddition of acylethynylpyrroles with diethyl aminomalonate hydrochloride ( Scheme 1 b) [ 18 ].…”