A three-component reaction between trialkyl phosphites or triphenylphosphine,dimethyl acetylenedicarboxylate and N -aryl-3-hydroxynaphthalene–2-carboxamide

Abstract

A three-component reaction between dimethyl acetylenedicarboxylate (DMAD) and trialkyl phosphites in the presence of N-aryl-3-hydroxynaphthalene-2-carboxamide leads to dialkyl 2-(dimethoxyphosphoryl)-3-[2-hydroxy-3-(arylcarbamyl)naphthalen-1-yl] succinate in excellent yields. A similar reaction with triphenylphosphine, instead of phosphites, produces dimethyl 2-[2-hydroxy-3-(arylcarbamoyl)naphthalen-1-yl]maleates. In the absence of triphenylphosphine or phosphite, DMAD adds to N-aryl-3-hydroxynaphthalene-2-carboxamide to produce alkyl 2-(alkoxycarbonylmethyl)-4-oxo-3-aryl-3,4-dihydro-2H-naphtho[2,3-e][1,3]oxazine-2-carboxylates in good yields.