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Microwave Assisted, 4-dimethylaminopyridine (DMAP) Mediated, Onepot, Three-component, Regio- and Diastereoselective Synthesis of Trans- 2,3-dihydrofuro[3,2-c]coumarins

[ Vol. 1 , Issue. 2 ]

Author(s):

Nanabhau B. Karanjule and Shriniwas D. Samant   Pages 135 - 141 ( 7 )

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 (140°C, 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.

Keywords:

2-Bromo-1-phenylethanone, 4-dimethylaminopyridine, 4-hydroxycoumarins, diastereoselective reaction, green synthesis, microwave assisted synthesis, multicomponent reaction, N-ylides, regioselective reaction, one-pot reaction, threecomponent reaction, trans-2, 3-dihydrofuro[3, 2-c]coumarins.

Affiliation:

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

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