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Paper | Regular issue | Vol 92, No. 1, 2016, pp.75-85
Published online, 18th December, 2015
DOI: 10.3987/COM-15-13360
Facile and Efficient Access to Tetrahydrobenzo[b]pyrans Catalyzed by N,N-Dimethylbenzylamine

Hamzeh Kiyani* and Mozhgan Sadat Jalali

*School of Chemistry, Damghan University, 36719-41167 Damghan, Iran

Abstract

The N,N-dimethylbenzylamine (DMBA) has been used as an efficient, inexpensive, and commercially available organocatalyst for the one-pot, three-component synthesis of tetrahydrobenzo[b]pyrans in good to high yields. It was found that the one-pot Knoevenagel-Michael-Thorpe-Ziegler cyclization sequence of dimedone, malononitrile/ethyl cyanoacetate, and various aldehydes was efficiently implemented in ethanol at 45 °C. This procedure offers attractive several features: mild reaction conditions, use of ethanol as a green solvent, reusability the reaction media, shorter reaction times, and the ease of the work-up.