A microwave-assisted facile one-pot synthesis of annelated pyridines from β-formyl enamides via Henry reaction

A Chetia, M Longchar, KC Lekhok, RC Boruah

Index: Chetia, Apurba; Longchar, Moanochet; Lekhok, Kushal C.; Boruah, Romesh C. Synlett, 2004 , # 7 p. 1309 - 1311

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Citation Number: 9

Abstract

In a typical reaction, steroidal β-formyl enamide (1) and nitromethane were mixed with pyrrolidine and irradiated in a Synthwave Microwave Module 402 (Prolabo) at operating frequency of 2450 MHz and 80% of output power for 8-10 minutes (Scheme [1] ). The work up of the reaction mixture did not afford the expected nitro-aldol or nitro-olefin product; rather it afforded a cyclised product 5′-nitro-6′-methyl-pyrido-(17,16-b)-androst-5-ene (10) in 90% yield. The product was ...