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Paper | Special issue | Vol 73, No. 1, 2007, pp.795-804
Published online, 18th September, 2007
DOI: 10.3987/COM-07-S(U)59
One-Pot Formation of Functionalised 2-Piperidinones from Arylidenecyanoacetates and Methanolic Ammonia via Tandem Reactions

Manas Chakrabarty,* Sulakshana Karmakar, Shiho Arima, and Yoshihiro Harigaya

*Department of Chemistry, Bose Institute, 93/1, A.P.C. Road, Kolkata 700009, India

Abstract

Aryl aldehydes react with ethyl cyanoacetate in methanolic ammonium acetate to expeditiously furnish, besides high yields of arylidenecyanoacetates, 4,6-diaryl-3,5-dicyano-5-ethoxycarbonyl-2-piperidinones in low yields. But preformed arylidenecyanoacetates react with methanolic ammonia to furnish the same functionalised 2-piperidinones in much better yields. The actual stereostructure of one of the products was determined by single crystal X-ray diffraction analysis, and novel tandem reactions occurring in one pot are proposed for the formation of the products.