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Synthesis of 2,4‐Diaryl‐1,3‐benzoxazines via FeCl 3 ‐Catalyzed Annulation of ortho ‐Hydroxyphenyl‐Substituted para ‐Quinone Methides with Imidates
Author(s) -
Zhang JingRu,
Jin HaiShan,
Wang RuBing,
Zhao LiMing
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201900842
Subject(s) - annulation , chemistry , quinone , catalysis , combinatorial chemistry , reaction conditions , transformation (genetics) , organic chemistry , biochemistry , gene
A strategy has been established for the synthesis of 2,4‐diaryl‐1,3‐benzoxazines via a FeCl 3 ‐catalyzed annulation of ortho ‐hydroxyphenyl‐substituted para ‐quinone methides ( p ‐QMs) and imidates. This transformation proceeds under mild, operationally‐simple conditions in a very short time. A wide range of substrates was accessed in this facile chemical transformation, in which the cyclized products were isolated in good to excellent yields (37% to 98%). This reaction not only provides an efficient method for the construction of biologically important 2,4‐diaryl‐1,3‐benzoxazines but also greatly enriches the chemistry of p ‐QMs.