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

Sreenivas, Kukkamudi and Khan, Faiz Ahmed (2019) 1,6-Conjugate addition of C-nucleophiles to p-quinone methide surrogate: Synthesis of diarylpropanes. Tetrahedron, 75 (5). pp. 633-642. ISSN 0040-4020

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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.

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IITH Creators:	IITH Creators ORCiD Khan, Faiz Ahmed UNSPECIFIED
Item Type:	Article
Uncontrolled Keywords:	1,3-Diarylpropanes, 1,6-Conjugate addition, Para-quinone methide surrogate, Carbon nucleophiles, Halophilic substitution
Subjects:	Chemistry
Divisions:	Department of Chemistry
Depositing User:	Team Library
Date Deposited:	04 Jan 2019 06:55
Last Modified:	14 Jan 2019 05:36
URI:	http://raiithold.iith.ac.in/id/eprint/4656
Publisher URL:	http://doi.org/10.1016/j.tet.2018.12.048
OA policy:	http://www.sherpa.ac.uk/romeo/issn/0040-4020/
Related URLs:	Google Scholar

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