Beilstein Journal of Organic Chemistry 2014-01-01

A catalyst-free multicomponent domino sequence for the diastereoselective synthesis of (E)-3-[2-arylcarbonyl-3-(arylamino)allyl]chromen-4-ones.

Pitchaimani Prasanna, Pethaiah Gunasekaran, Subbu Perumal, J Carlos Menéndez

Index: Beilstein J. Org. Chem. 10 , 459-65, (2014)

Full Text: HTML

Abstract

The three-component domino reactions of (E)-3-(dimethylamino)-1-arylprop-2-en-1-ones, 3-formylchromone and anilines under catalyst-free conditions afforded a library of novel (E)-3-(2-arylcarbonyl-3-(arylamino)allyl)-4H-chromen-4-ones in good to excellent yields and in a diastereoselective transformation. This transformation generates one C-C and one C-N bond and presumably proceeds via a reaction sequence comprising a Michael-type addition-elimination reaction, a nucleophilic attack of an enamine to a carbonyl reminiscent of one of the steps of the Bayllis-Hilman condensation, and a final deoxygenation. The deoxygenation is assumed to be induced by carbon monoxide resulting from the thermal decomposition of the dimethylformamide solvent.