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

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.

SUBMITTER: Prasanna P

PROVIDER: S-EPMC3944430 | biostudies-literature | 2014

REPOSITORIES: biostudies-literature

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

Prasanna Pitchaimani P Gunasekaran Pethaiah P Perumal Subbu S Menéndez J Carlos JC

Beilstein journal of organic chemistry 20140221

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 enami ...[more]

PMID: 24611080

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