An efficient, one-pot three components synthesis of [1,2,4] triazoloquinazolinone derivatives using anthranilic acid as green catalyst

Aminoazole-Based Diversity-Oriented Synthesis of Heterocycles

“…The analogous to heterocycles 7 linear quinazolinones 10 were obtained on the basis of 3-amino-1,2,4-triazole ( 5a ) applying the great variety of conditions (only the endocyclic aminogroup in the position 2 took part in the condensation; Puligoundla et al, 2013 ; Petrov and Kasatochkin, 2014 ; Sompalle et al, 2016 ; Vibhute et al, 2017a , b ). It should be noted, that in all cases tetrahydroderivatives 6 – 10 were formed.…”

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“…Hamidi and co-worker, synthesized thio-and oxazepino [7,6-b]quinolones and evaluated their anti-bacterial activity [27]. Vibhute et al synthesized [1,2,4] triazoloquinazolinone derivatives using anthranilic acid as green catalyst [28]. Also El-Hashash and co-worker, prepared novel quinazoline derivatives using 2-Ethoxyquinazolin-4-yl hydrazine and evaluated their antimicrobial activity [29].…”

“…Also El-Hashash and co-worker, prepared novel quinazoline derivatives using 2-Ethoxyquinazolin-4-yl hydrazine and evaluated their antimicrobial activity [29]. Among various chemical approaches, one-pot, multicomponent reactions have gained significant importance due to their high yielding, clean, and eco-friendly approach, which became the current area of interest in medicinal chemistry research [8][9][10][11][12][13].…”

Tetramethylguanidine-functionalized melamine as a multifunctional organocatalyst for the expeditious synthesis of 1,2,4-triazoloquinazolinones

“…Among various reported procedures for the synthesis of 1,2,4-triazoloquinazolinone derivatives, the three-component reaction of enolizable 1,3-dicarbonyls, 3-amino-1,2,4-triazole, and aldehydes/ketones has been known as the most beneficial method in terms of obtained yield, selectivity and green chemistry principles 51 , 56 – 66 . Some recent examples include DABCO based ionic liquid 67 , TiO 2 nanoparticles supported ionic liquids 68 , magnetic nanoparticles coated by silica with bis dicationic bridge 69 , sulfonic acid functionalized SBA-15 70 , nanoporous silica 71 , H 4 [W 12 SiO 40 ] grafted on magnetic chitosan 72 , l -proline 51 , p -toluenesulfonic acid monohydrate 73 , sulfamic acid 74 , anthranilic acid 75 , molecular iodine 76 , etc 77 , 78 . However, there is a lot more room to explore new and more efficient catalytic systems for this MCR which can work under green conditions using organocatalytic systems.…”