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Facile One‐Pot Synthesis of Methyl 1‐Aryl‐1 H ‐1,2,4‐triazole‐3‐carboxylates from Nitrilimines with Vilsmeier Reagent
Author(s) -
Tsai ShuoEn,
Chiang KunHeng,
Tseng ChingChun,
Chen NaiWei,
Chern ChingYuh,
Wong Fung Fuh
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801808
Subject(s) - chemistry , reagent , cycloaddition , aryl , combinatorial chemistry , amine gas treating , intramolecular force , medicinal chemistry , substrate (aquarium) , trimethylsilyl , organic chemistry , catalysis , alkyl , oceanography , geology
Two convenient and effective one‐pot methods have been developed to synthesize methyl 1‐aryl‐1 H ‐1,2,4‐triazole1–3‐carboxylates by using hydrazonoyl hydrochlorides (nitrilimines) with Vilsmeier reagent. The first, a direct one‐pot method, involved the reaction between nitrilimines and Vilsmeier reagent at 85 °C for about 0.5 h. Another one‐pot two‐step cascade method proceeded via nucleophilic substitution with bis(trimethylsilyl)amine [NH(SiMe 3 ) 2 ] and subsequent intramolecular cycloaddition reaction with Vilsmeier reagent. Substrate scope, multicomponent examples, and mechanistic insights are discussed.