Abstract
Herein, Sonogashira coupling at the vinyl bromide position of triazole-bearing benzosuberene
has been introduced for the synthesis of potentially bioactive 1,2,3-triazole and
conjugated enynes containing benzosuberene analogues. The instalment of triazole moiety
on the allylic position dictates the Sonogashira coupling at the vinylic position,
the absence of which failed to execute the desired reaction. The Cu-catalyzed cycloaddition
initially led to the incorporation of 1,2,3-triazole, which subsequently directed
the Pd/Cu-catalyzed Sonogashira coupling to deliver new class of benzosuberene analogues
in appreciable yields. The regioselective synthesis of 1,2,3-triazole and conjugated
enynes containing benzosuberene analogues has been reported under operationally simple
and milder reaction conditions.
Keywords
Cedrus deodara oil - cycloaddition reaction - Sonogashira coupling - 1,2,3-triazoles synthesis -
enynes synthesis - benzosuberene analogues
