title: 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.
authors.affiliation: Department of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai - 625 021, Tamilnadu, India.
authors.forename: Pitchaimani
authors.initials: P
authors.lastname: Prasanna
authors.affiliation: Department of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai - 625 021, Tamilnadu, India.
authors.forename: Pethaiah
authors.initials: P
authors.lastname: Gunasekaran
authors.affiliation: Department of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai - 625 021, Tamilnadu, India.
authors.forename: Subbu
authors.initials: S
authors.lastname: Perumal
authors.affiliation: Departamento de Química Orgánica and Farmacéutica, Facultad de Farmacia, Universidad Complutense, 28040 Madrid, Spain.
authors.forename: J Carlos
authors.initials: JC
authors.lastname: Menéndez
keywords: Michael additions; chromones; domino reactions; multicomponent reactions; transfer hydrogenation