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1,6-Conjugate addition of C-nucleophiles to p-quinone methide surrogate: Synthesis of diarylpropanes

Author:
Sreenivas, Kukkamudi, Khan, Faiz Ahmed
Source:
Tetrahedron 2019 v.75 no.5 pp. 633-642
ISSN:
0040-4020
Subject:
Lewis bases, carbon, dimerization, moieties, nitroalkanes, phenol, quinones
Abstract:
1,6-Conjugate addition of various carbon nucleophiles to p-quinone methide surrogate is reported. The active methylene containing C-nucleophiles such as 1,3-diketones, diesters and ketoesters underwent two consecutive additions leading to bis-addition products, diarylpropanes. Whereas, nitroalkanes proceeded to contribute mono-addition products. Surprisingly, bromo analogue of p-quinone methide surrogate underwent halophilic dimerization reaction with excellent yield. The reported strategy provides an efficient synthesis of 1,3-diarylpropane derivatives bearing pharmacophoric ortho-methoxy phenol moiety under mild reaction conditions.
Agid:
6289863