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Indium(III) Chloride Promoted One‐Pot Multicomponent Synthesis of 1,2,4‐Triazole Carrying 1,2,4‐Triazin‐6‐ones from Nitrile Imines and N , N′ ‐Bis(trimethylsilyl)carbodiimine
Author(s) -
Tsai ShuoEn,
Yen WanPing,
Li YiTing,
Hu YuTzu,
Tseng ChingChun,
Wong Fung Fuh
Publication year - 2017
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.201700271
Subject(s) - chemistry , nitrile , trimethylsilyl , imine , cycloaddition , chloride , medicinal chemistry , indium , combinatorial chemistry , organic chemistry , catalysis
An indium(III) chloride/silica gel promoted one‐pot multicomponent reaction for the synthesis of 5‐[2‐(1,2,4‐triazol‐3‐yl)hydrazinyl]‐1,2,4‐triazin‐6‐ones was developed by treating hydrazonoyl hydrochlorides with N , N′ ‐bis(trimethylsilyl)carbodiimine. The first step of the reaction mechanism involves the promotion of the 1,3‐dipolar cycloaddition by indium(III) chloride/silica gel. The subsequent cyclization and substitution reaction sequence employs 2 equiv of the nitrile imine and the silylamide intermediate, which may be the key species, to lead to the product.