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Silver‐Promoted [3+1+1] Annulation of Isocyanoacetates with Nitrosoarenes
Author(s) -
Fang Guichun,
Wang Hongwei,
Liu Qun,
Cong Xuefeng,
Bi Xihe
Publication year - 2018
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201800172
Subject(s) - annulation , chemistry , aromatization , catalysis , yield (engineering) , combinatorial chemistry , medicinal chemistry , organic chemistry , materials science , metallurgy
[3+1+1] annulation of isocyanoacetates with nitrosoarenes for the preparation of 1,4,5‐trisubstituted imidazoles or 4,5‐dihydro‐1 H ‐imidazoles has been disclosed. Isocyanoacetates serve as both a three‐atom component and a one‐carbon unit in the reaction. Specially, with catalytic amounts of Ag 2 CO 3 and a reduced temperature this [3+1+1] annulation of isocyanoacetates enables the formation of trans ‐imidazolines in good yield and with high diastereoselectivity. Silver plays a critical dual role: i) as the catalyst for the efficiency to activate the isocyanides and ii) the oxidant in aromatization process.