Synfacts 2011(4): 0371-0371  
DOI: 10.1055/s-0030-1259753
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Furo[3,2-c]pyridinones via an Aza-Oxy-Carbanion Relay Strategy

Contributor(s): Victor Snieckus, Timothy Hurst
F. Liang*, S. Lin, Y. Wei
Northeast Normal University, Changchun, P. R. of China
Further Information

Publication History

Publication Date:
18 March 2011 (online)


Reported is the synthesis of furo-[3,2-c]pyridinones 3 from 1-cinnamoylcyclopropanecarboxamides 1 with aldehydes 2, which proceeds via a proposed aza-oxy-carbanion relay process. Both electron-rich and -poor aromatic groups are tolerated in reactant 1. Aromatic and alkenyl aldehydes 2 participate equally well, although aliphatic aldehydes lead to decomposition. Chalcones were also shown to be efficient electrophiles, giving rise to compounds 4 in excellent yield. However, the use of simpler electrophiles (BnBr, MeI, TMSCl) proved unsuccessful. A mechanism is proposed involving a Michael addition/cyclopropane ring opening/anion migration/electrophile quench cascade.