Abstract
A novel series of isoindolinotriazole derivatives with different substituents in the triazole moiety were synthesized via copper-catalyzed cycloaddition (CuAAC) click chemistry between 2-(meta- or para-ethynylphenyl)-4,6-dimethoxyisoindolin-1-ones and several azides. The synthesized triazoles were characterized by IR, 1H NMR, 13C NMR and mass spectral techniques.
Highlights
Isoindolinones are interesting heterocyclic compounds due to their presence in many naturally occurring substances [1,2] and because of their extensive biological properties such as antihypertensive [3], antipsychotic [4] anxiolytic [5] and antiviral [6].In medicinal chemistry, the triazoles are known to possess a number of desirable features including sufficient stability to acidic/basic hydrolysis and reductive/oxidative conditions, indicative of a high aromatic stabilization [7]
The triazoles are known to possess a number of desirable features including sufficient stability to acidic/basic hydrolysis and reductive/oxidative conditions, indicative of a high aromatic stabilization [7]
Tazobactam, a b-lactamase inhibitor is among the best-known examples of triazole containing structures with the broad-spectrum antibiotic piperacillin [8]
Summary
Isoindolinones are interesting heterocyclic compounds due to their presence in many naturally occurring substances [1,2] and because of their extensive biological properties such as antihypertensive [3], antipsychotic [4] anxiolytic [5] and antiviral [6].In medicinal chemistry, the triazoles are known to possess a number of desirable features including sufficient stability to acidic/basic hydrolysis and reductive/oxidative conditions, indicative of a high aromatic stabilization [7]. We report the high-yielding synthesis of novel isoindolinotriazoles 3a-h using 1,3-dipolar cycloaddition reaction of ethynylisoindolinones 2a-b with several azides in the presence of Cu(I) catalyst at room temperature.
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