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

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.