CSIR – National Institute for Interdisciplinary Science and Technology (NIIST)

Council of Scientific & Industrial Research (CSIR), Govt.Of India Thiruvananthapuram.

Catalyst controlled straightforward synthesis of highly substituted pyrroles/furans via propargylation/cycloisomerization of α-oxoketene-N,S-acetals

DOI: 10.1021/acs.joc.6b02367

Ganesh Chandra Nandi* and Soumini K.

Abstract A facile and efficient InCl3 catalyzed one-pot synthesis of highly substituted pyrroles has been developed via a tandem propargylation/cycloisomerization reaction of α-oxoketene-N,S-acetals with propargyl alcohols. Notably, in the presence of Bronsted acid p-TSA.H2O, the reaction afforded the hydrolyzed product propargylated-1,3-dicarbonyl compounds, which upon treatment with Cs2CO3 underwent regioselective intramolecular cyclization furnishing tetrasubstituted furan derivatives.