Abstract
Ugi-azide four-component reaction (UA-4CR) as development on Ugi four-component reaction (U-4CR) is the condensation reaction involving an aldehyde, an amine, an isocyanide, and an azide source. Nowadays, UA-4CR has been employed for the efficient and facile production of 1,5-disubstituted-1H-tetrazoles (1,5-DS-1H-Ts). Interestingly, the combination of 1,5-DS-1H-Ts with suitable post-transformations in a tandem manner results in the construction of various classes of heterocyclic compounds bearing 1,5-DS-1H-T moiety. This review aims to provide the application of diverse post-Ugi-azide reaction in the preparation of different N-heterocyclic compounds bearing 1,5-DS-1H-T such as substituted and fused 1,5-DS-1H-Ts.
Highlights
In 1885, tetrazole was synthesized and characterized by the Swedish chemist, Bladin at the University of Upsala through the reaction of the anhydrous hydrazoic acid with hydrogen cyanide under pressure [1]
We have reported applications of isocyanide-based multicomponent reactions (IMCRs) [45,46,47]
The UA-4CR is one of the essential and useful IMCRs which was discovered by Ivar Karl
Summary
In 1885, tetrazole was synthesized and characterized by the Swedish chemist, Bladin at the University of Upsala through the reaction of the anhydrous hydrazoic acid with hydrogen cyanide under pressure [1]. One of the most important and well-established IMCRs is Ugi four-component reaction (U-4CR) which was discovered in 1959 by an Estonian-born German chemist, Ivar Karl Ugi and reported in Angewandte Chemie for the rapid and facile construction of an N-substituted acyl aminoamide via condensation of an amine, an isocyanide, an aldehyde, and a carboxylic acid. Nowadays, this reaction is known as Ugi four-component reaction (U-4CR) [22]. 1,5-DS-1H-Ts can be prepared using various imines through Ugi-azide three-component reaction (UA-3CR) [28]
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