Facile one-pot synthesis of chromeno[4,3-b]quinoline derivatives catalyzed by Cu(II)-Schiff base/SBA-15

Abstract

A novel, one-pot, simple, environmentally benign and efficient protocol has been employed for the synthesis of chromeno[4,3-b]quinoline derivatives in the presence of catalytic amounts of Cu(II)-Schiff base/SBA-15 under solvent-free conditions in excellent yields and rates.

Cu(II)-Schiff base/SBA-15 as an efficient catalyst for synthesis of decahydroacridine-1,8-diones

“…In our continued interest in the development of a highly expedient methodology [10,[13][14][15] for the synthesis of fine chemicals and heterocyclic compounds of biological importance, we report here the synthesis of decahydroacridine-1,8-diones, in the presence of Cu(II)-schiff base-SBA-15 as a reusable heterogeneous catalyst (Scheme 2).…”

“…Therefore, the discovery of new and inexpensive catalysts for the preparation of 1,4-DHPs is of prime importance. As part of our continuing interest in the development of new synthetic methodologies [10], we report herein an efficient and convenient procedure for the synthesis of 1,4-DHPs in the presence of Cu(II)-schiff base/SBA-15 catalyst.…”

Greener organic synthetic methods: Sonochemistry and heterogeneous catalysis promoted multicomponent reactions

“…A strategy well aligned with the green chemistry principles and which has been gaining prominence in recent years in the field of heterogeneous catalysis is the immobilization of nanoparticles (NPs) on solid supports, such as porous silica [85] , [86] , [87] , [88] , [89] , zeolites [84] , [90] , [91] , [92] , [93] , polymers [94] , [95] , [96] and carbon-based supports, including carbon nanotubes (CNTs) [97] , [98] , [99] , [100] , graphene [101] , [102] , [103] , graphene oxide (GO) [104] , [105] and graphene nanosheets (GNSs) [103] , [106] . A notable peculiarity of many of these supports – as is the case with graphene - is the property of having the surface easily modifiable, which is only possible due to the presence of large points of nucleation or stabilization [103] .…”

Nicotinic acid‐supported cobalt ferrite‐catalyzed one‐pot synthesis of substituted chromeno[3,4‐b]quinolines

“…Aminocoumarin derivatives have a wide range of biological applications, such as antibiotics, fluorescent markers, melanin‐concentrating hormone receptor antagonist, inducing estrogenic activity, carbonic anhydrase class of inhibitors, and α‐glucosidase inhibitors . Organic compounds containing 4‐aminocoumarin scaffold are synthesized by the reaction of 4‐hydroxycoumarin, ammonia solution, Meldrum's acid, and aromatic aldehydes in the presence of SBA‐15‐SO 3 H; three‐component reaction of 4‐aminocoumarin, arylglyoxal monohydrates, and aromatic amines promoted by KHSO 4 in toluene under reflux condition; three‐component condensation of 4‐aminocoumarin, aldehydes, and ethyl benzoylacetates by POCl 3 in dichloroethane under reflux conditions; three‐component domino condensation of 4‐ aminocoumarins, arylglyoxal monohydrates, and various nucleophilic substrates, such as arylamines, malononitrile, ethyl cyanoacetate, and cyanoacetamide‐produced functionalized chromeno[4,3‐ b ]pyrrol‐4(1 H )‐ones in the presence of Fe 3 O 4 @SiO 2 ‐SO 3 H nanoparticles as a solid acid catalyst under solvent‐free conditions; oxidative aromatization of tetrahydrochromeno[4,3‐ b ]quinoline derivatives by nitric acid at ambient temperature; two‐component coupling of 4‐aminocoumarin and α,β‐unsaturated nitroalkene catalyzed by PEG–SO 3 H; three‐component reaction of phenyl glyoxal, dimedone, and 4‐amino coumarin to afford disubstituted chromeno[4,3‐ b ]pyrrole‐4(1 H )‐one derivatives catalyzed by I 2 /dimethyl sulfoxide (DMSO); synthesis of coumarin fused to highly decorated indenodihydropyridyl and dihydropyridyl derivatives in the presence of (±)lactic acid/ethyl‐ l ‐lactate at 100 °C; and synthesis of chromeno[4,3‐ b ]quinoline derivatives in the presence of catalytic amounts of Cu(II)–Schiff base/SBA‐15 by condensation of arylaldehydes with 1,3‐cyclohexadione and then treating the obtained intermediates with 4‐aminocoumarin in an autoclave at 200 °C . Despite the potential utility of these methods, some suffer from disadvantages such as long reaction times, low yields, high reaction temperature, and the use of more corrosive catalyst.…”