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A three-component reaction of phosphorus ylides with isocyanates: facile synthesis of 2-amino-3-carboxylate-4-quinolones.

A three-component reaction between one molecule of phosphorus ylides (P-ylides) and two molecules of isocyanates for the rapid assembly of 2-amino-3-carboxylate-4-quinolones is described. The mechanism may involve the addition of a P-ylide to an isocyanate followed by 1,3-H shift to form a carbamoyl stabilized P-ylide. The intermediate then reacts with another aryl isocyanate via Wittig/ketenimine-ketene rearrangement/6π-electrocyclization/1,3-H shift to finally afford the 4-quinolones.