4602-93-1

Upstream product

• 762-42-5 dimethyl acetylenedicarboxylate 
• 108-95-2 phenol 

Relevant academic research and scientific papers

DABCO-catalyzed reaction of phenols or 1,2-diphenols with activated alkynes leading to the formation of alkenoic acid esters or 1,3-dioxole derivatives

The reaction of phenols or 1,2-diphenols with activated alkynes took place smoothly and rapidly in the presence of a catalytic amount of 1,4-diazabicyclo[2.2.2]octane (DABCO) at room temperature and resulted in the formation of various alkenoic acid ester

Trimethylamine catalyzed stereoselective reaction between dimethyl acetylenedicarboxylate and phenols

Stereoselective reaction of various substituted phenols with dimethyl acetylenedicarboxylate in the presence of a catalytic amount of aqueous trimethylamine solution in dichloromethane leads to dimethyl 2-phenoxymaleates in good to excellent yields under mild condition.

A Selective and Versatile Synthesis of Substituted Chromones via Addition of Phenols to Dimethyl Acetylenedicarboxylate

Despite many published syntheses of chromones, none has been reported to be both selective for chromones and tolerant of ring substitution.The addition of substituted phenols to dimethyl acetylenedicarboxylate is now reported as a versatile high yield initial step in a simple three-step synthesis of chromone 2-carboxylic acids.Triethylamine being used to deprotonate the substituted phenol, the addition to dimethyl acetylenedicarboxylate proceeds under mild conditions and tolerates a wide range of functional groups on the phenol.Although not stereoselective, both fumarate and maleate aryloxy products of this addition can then be cyclized, according to a known method, to chromones without contamination by isomeric coumarins.Thus the addition reaction is a valuable component of a versatile and selective synthesis of substituted chromones.

Stereoselective Addition of Phenols to Dimethyl Acetylenedicarboxylate adsorbed on Alumina

Although phenols react with dimethyl acetylenedicarboxylate (DMAD) to give a mixture of both cis- and trans-addition products, the reaction with DMAD adsorbed on alumina gives cis-addition products stereoselectively.