Synthesis of bioactive heterocycles: tandem reaction of 4- N-(4′-aryloxybut-2′-ynyl), N-methylaminocoumarin with 3-chloroperoxybenzoic acid

Abstract

A number of 4- N-(4′-aryloxybut-2′-ynyl), N-methylaminocoumarins ( 4a– e ) on treatment with one equivalent of 3-chloroperoxybenzoic acid at 0–5°C for 10 min and then stirring at rt for 10 h afforded pyrrolo[3,2- c]coumarin derivatives in 70–75% yields. The 4- N-(4′-aryloxybut-2′-ynyl), N-methylaminocoumarins 4a– e were in turn prepared from 4-tosyloxycoumarin ( 2 ) and (4-aryloxybut-2-ynyl)- N-methylamine ( 3a– e ).