Switchable pathways of multicomponent heterocyclizations of 5-amino-1,2,4-triazoles with salicylaldehydes and pyruvic acid
Yana I Sakhno, Oleksander V Buravov, Kostyantyn Yu Yurkov, Anastasia Yu Andryushchenko, Svitlana V Shishkina, Valentyn A Chebanov
TL;DR
This paper shows how changing reaction conditions can switch the products formed from the same starting chemicals.
Contribution
The study demonstrates a switchable pathway in multicomponent reactions using triazoles, pyruvic acid, and salicylaldehydes.
Findings
Conventional heating produces benzotriazolooxadiazocine-5-carboxylic acids.
Ultrasonic activation or room temperature stirring yields tetrahydrotriazolopyrimidine derivatives.
Abstract
Switchable multicomponent reactions involving 3-substituted-5-amino-1,2,4-triazoles, pyruvic acid, and salicylaldehydes were studied under different conditions. Upon conventional heating, benzotriazolooxadiazocine-5-carboxylic acids were formed in the three-component reactions as single reaction products. Upon ultrasonic activation or mechanical stirring at room temperature, the multicomponent reaction of the same starting materials led to the formation of only tetrahydrotriazolopyrimidine derivatives.
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Taxonomy
TopicsMulticomponent Synthesis of Heterocycles · Synthesis and Characterization of Heterocyclic Compounds · Synthesis and biological activity