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Updated: Jun 23, 2025

Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
1,6-Conjugate addition of in situ generated aryldiazenes to p-quinone methides
Ajay G Mamale1,2, Sayantan Paul1,2, Rajesh G Gonnade2,3
1Division of Organic Chemistry, CSIR-National Chemical Laboratory (CSIR-NCL), Dr. Homi Bhabha Road, Pune-411 008, India. ak.bhattacharya@ncl.res.in.
Abstract:
Herein we report a transition-metal free, base-mediated 1,6-conjugate addition of aryldiazenes to para-quinone methides (p-QMs). Arylhydrazines were used for the in situ generation of aryldiazenes using a base-mediated protocol in the presence of air as the oxidant. The 1,6-conjugate addition of aryldiazenes to para-quinone methides via a radical mechanism is followed by an oxidative rearrangement to furnish the desired product, arylhydrazones. Interestingly, our synthetic protocol results in the formation of an aryldiazene radical, which undergoes 1,6-conjugate addition with p-QMs to furnish the arylhydrazones.
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