Facial and Efficient Access to Dihydropyrano[3,2-c]Chromenes via Three-Component Reaction Using N,N-Dimethylbenzylamine As a New Organocatalyst

Author(s): Hamzeh Kiyani, Mozhgan Sadat Jalali.

Journal Name: Combinatorial Chemistry & High Throughput Screening
Accelerated Technologies for Biotechnology, Bioassays, Medicinal Chemistry and Natural Products Research

Volume 19 , Issue 4 , 2016

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Abstract:

The N,N-dimethylbenzylamine (DMBA), as an efficient and commercially available organocatalyst was employed for the one-pot synthesis of dihydropyrano[3,2-c]chromene derivatives in ethanol medium. In this work, the one-pot Knoevenagel-Michael-Thorpe-Ziegler type cascade heterocyclization has been developed for the synthesis of dihydropyrano[3,2-c]chromene-containing heterocycles from the one-pot multicomponent condensation reaction of 4-hydroxycoumarin, malononitrile/ethyl cyanoacetate, and various aldehydes at 60°C. The salient features of this basecatalyzed reaction are mild reaction conditions, reusability of the reaction medium, shorter reaction times, and easy separation of the reaction mixture.

Keywords: Dihydropyrano[3, 2-c]chromenes, N, N-Dimethylbenzylamine, 4-Hydroxycoumarin, Knoevenagel condensation, Nitrile-containing compounds, Three-component annulation.

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Article Details

VOLUME: 19
ISSUE: 4
Year: 2016
Page: [275 - 282]
Pages: 8
DOI: 10.2174/1386207319666160310144315
Price: $58

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