923121-28-2

Usage

Structure

Contains a benzene ring and a pyran ring fused together

Functional groups

Ethoxy group and carboxylic acid group attached to the chromene ring

Potential applications

Pharmaceutical industry for the development of new drugs, organic synthesis, chemical research

Unique features

Interesting chemical properties and reactivity, potential biological activities in drug development

Upstream product

• 548756-57-6 tert-butyl 3-(3-ethoxy-2-hydroxyphenyl)-3-hydroxy-2-methylenenpropanoate 

Relevant academic research and scientific papers

Strong base- or acid-mediated chemoselectivity shifts in the synthesis of 2H-chromene or coumarin derivatives from common Baylis-Hillman adducts

Abstract Reaction of tert-butyl 3-(2-hydroxyphenyl)-2-methylenepropanoate esters with aqueous KOH provides convenient and chemoselective one-pot access to 2H-chromene-3-carboxylic acids, the overall transformation involving tandem conjugate addition, hydrolysis and elimination steps. The methodology complements the chemoselective, acid-catalysed route to 3-substituted coumarins from the same substrates by switching the regioselectivity of cyclisation.