Sonochemical synthesis of pyrido[2,3-d:6,5-d′]-dipyrimidines catalyzed by [HNMP]+[HSO4]− and their antimicrobial activity studies

Abstract

In this study, the one-pot four-component reaction of aromatic aldehyde, 2-thiobarbituric acid, ammonium acetate in the presence of a catalytic amount of [H-NMP][HSO] under ultrasonic irradiation in water is reported. In the present procedure, the pyrido[2,3-d:6,5-d']dipyrimidine derivatives were purely produced as valuable products. The process proved to be simple, environmentally friendly, efficient and high to excellent yielding. Moreover, some of the synthetic compounds were investigated and revealed important antimicrobial activity of prepared products.

One‐pot synthesis of pyrido[2,3‐d:5,6‐d′]dipyrimidines using CoFe2O4@SiO2‐PA‐CC‐guanidine‐SA magnetic nanoparticles in water

“…We are grateful of Ilam University for the financial support of this work. Naeimi and Didar [31] 2 [H-NMP] + [HSO 4 ] À H 2 O, ultrasonic 5 98 Naeimi et al [29] 3 Fe-MCM-41-IL H 2 O, r.t 34 91 Naeimi et al [32] 4…”

An overview on synthetic and pharmaceutical prospective of pyrido[2,3‐d]pyrimidines scaffold

“…Naeimi and co-workers synthesized an effective and appropriate pyrido [2,3-d: 6,5-d′] dipyrimidine derivatives through simple one pot, multicomponent reaction protocol of 2-thiobarbiturate, ammonium acetate and substituted aromatic aldehyde by condensation in the presence of [H-NMP] + [HSO 4 ] − as a catalyst. The synthesized compounds 32a-32j were evaluated and revealed significant antimicrobial activity (Naeimi et al, 2017). Gao et al developed the synthesis of pyrido[2,3-d]pyrimidine derivatives and figured out as new potent inhibitors of HIV integrase.…”

Ecofriendly and Facile One‐Pot Multicomponent Synthesis of 5‐Phenyl‐5,10‐dihydropyrido[2,3‐d : 6,5‐d′]dipyrimidine‐2,4,6,8(1H,3H,7H,9H)‐tetraone Derivatives Catalyzed by CuII Immobilized on Functionalized Magnetic Mesoporous MCM‐41 (Fe3O4@MCM‐41‐GPTMS‐Gu‐CuII)

“…[30] These heterocyclic compounds can selfassemble to constitute a supramolecular structure as well. [31] Therefore, many different strategies have been developed to synthesize various structures of 5-phenyl-5,10-dihydropyrido [2,3- [32][33][34] These techniques suffer particular drawbacks such as unwanted by-products, using organic solvents, base, heating and/or refluxing condition, and ultrasound irradiation or tedious procedure of catalyst preparation, which are not in agreement with the green chemistry strategies. Consequently, in order to overcome these kinds of problems, a continued pursuit for reaching greener, simpler, more convenient, and environmentallyfriendly approaches are still paramount.…”

“…In the meantime, an essential group of heterocyclic frameworks containing 1,4‐dihydropyridines core is 5‐phenyl‐5,10‐dihydropyrido[2,3‐d : 6,5‐d′]dipyrimidine‐2,4,6,8(1 H ,3 H ,7 H ,9 H )‐tetraone derivatives which have attracted considerable attention due to their broad spectrum of promising biological activities and medicinal applications [25] . Numerous reports represent anticorrosive, [26] antimicrobial, [27] antitubercular, [28] antiviral, and cytotoxic activities [29] of these compounds (Scheme 1). Moreover, a few numbers of such derivatives have significant α ‐glucosidase and α ‐amylase inhibitory activity [30] .…”

“…These heterocyclic compounds can self‐assemble to constitute a supramolecular structure as well [31] . Therefore, many different strategies have been developed to synthesize various structures of 5‐phenyl‐5,10‐dihydropyrido[2,3‐d : 6,5‐d′]dipyrimidine‐2,4,6,8(1 H ,3 H ,7 H ,9 H )‐tetraone derivatives such as using DIPEA, [H‐NMP] + [HSO 4 ] − ,γ‐Fe 2 O 3 @HAp‐SO 3 H, nano‐[DMSPDE][Cl], Fe‐MCM‐41‐ionic liquid, nano‐CuFe 2 O 4 , and CuFe 2 O 4 nanospheres [32–34] . These techniques suffer particular drawbacks such as unwanted by‐products, using organic solvents, base, heating and/or refluxing condition, and ultrasound irradiation or tedious procedure of catalyst preparation, which are not in agreement with the green chemistry strategies.…”