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Cascade substitution reaction between oxabornene and amines to construct cyclohexa‐1,4‐diene‐3,6‐diamine and amino alcohol
Author(s) -
Zhao Changkuo,
Wang Xianheng,
Xu Lang,
Cao Ying,
Cui Hanqi,
Wang Yuhe
Publication year - 2020
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.3917
Subject(s) - chemistry , alcohol , cascade reaction , diamine , diene , yield (engineering) , cascade , organic chemistry , michael reaction , medicinal chemistry , chromatography , catalysis , natural rubber , materials science , metallurgy
Abstract In competition with Michael addition between oxabornene and amines, a cascade substitution reaction predominates to generate cyclohexa‐1,4‐diene‐3,6‐diamine and amino alcohol in a moderate yield. This method has wide universality for different amines, overcomes the shortcomings of Michael addition reaction that cannot be synthesized due to shortage of raw materials, and can be further applied to the total synthesis of some related natural products.