Synfacts 2011(12): 1291-1291  
DOI: 10.1055/s-0031-1289407
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Metal-Free Synthesis of Pyrroles From Morita-Baylis-Hillman Acetates

Contributor(s): Victor Snieckus, Timothy Hurst
C. R. Reddy*, M. D. Reddy, B. Srikanth, K. R. Prasad
Indian Institute of Chemical Technology, Hyderabad, India
Further Information

Publication History

Publication Date:
18 November 2011 (online)

Significance

Reported is the synthesis of di­substituted pyrroles 3 by the reaction of Morita-Baylis-Hillman acetates 1 with amines 2 via a ­metal-free tandem allylic substitution-cycloiso­merization approach. Both aliphatic and aromatic amines participate efficiently in the reaction. Primary sulfonamides may also be used, allowing ­access to N-unsubstituted pyrroles by desulfo­nylation. In terms of the Morita-Baylis-Hillman coupling partner, alkyl and aromatic R¹ substitution is tolerated, as is R¹ = H. Fused pyrroles 4 and 5 were also prepared by the same method. Limited mechanistic studies suggest that the initial allylic substitution must give the E-isomer for the cycloisomerization to proceed.