Microwave Assisted, 4-Dimethylaminopyridine (DMAP) Mediated, One-Pot, Three-Component, Regio- and Diastereoselective Synthesis of Trans-2, 3-Dihydrofuro [3, 2-c] Coumarins

ISSN: 2213-3364 (Online)
ISSN: 2213-3356 (Print)


Volume 1, 2 Issues, 2014






Current Microwave Chemistry

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Microwave Assisted, 4-Dimethylaminopyridine (DMAP) Mediated, One-Pot, Three-Component, Regio- and Diastereoselective Synthesis of Trans-2, 3-Dihydrofuro [3, 2-c] Coumarins

Author(s): Nanabhau B. Karanjule and Shriniwas D. Samant

Affiliation: Organic Chemistry Research Laboratory, Department of Chemistry, Institute of Chemical Technology, N.M. Parekh Road, Matunga, Mumbai 400 019, India.

Abstract

The regio- and diastereoselective base catalyzed one-pot, multicomponent reaction of 4-hydroxycoumarin, aldehyde, and 2-bromo-1-phenylethanone giving trans 2,3-dihydrofuro[3,2-c]coumarins is greatly accelerated by a combination of 4-(N,N-dimethylamino)pyridine (DMAP) and microwave heating. The classical thermal reaction takes a long reaction time and uses environment unfriendly bases, pyridine, NaOH. The microwave reaction is carried out in Biotage Synthesizer at different temperatures under built-in pressure. Among the organic and inorganic bases used, DMAP is the best base. Further, replacement of pyridine/NaOH by DMAP makes the reaction greener. Microwave irradiation (1400C, 4 bar) accelerates the reaction greatly as compared to its thermal counterpart. The effect of microwaves could be correlated with the dielectric loss of the polar solvents. 1-propanol and ethanol that have high dielectric loss are the best solvents under microwave irradiation. In the reaction DMAP functions as a nucleophile, a base, and a good leaving group. The method is highly regioselective, diastereoselective and gives good yield of the product.


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Article Details

Volume: 1
First Page: 1
Last Page: 1
Page Count: 1
DOI: 10.2174/2213335601666140529003616
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