An efficient contemporary multicomponent synthesis for the facile access to coumarin‐fused new thiazolyl chromeno[4,3‐b]quinolones in aqueous micellar medium

Abstract

Coumarin-fused polycyclic chromenoquinolone derivatives were synthesized in CTAB/water system with high yields. This protocol is competent, feasible, and sequential one-pot multicomponent path for the building of titled products. In this projected route solvents, catalysts and surfactants are optimized, and the excellent results were achieved by CTAB in water. CTAB/water has efficiently catalyzed the synthesis of new thiazolyl chromenoquinolone heterocycles and avoids the use of hazardous conventional organic solvents. The synthesized compounds were confirmed by IR, mass, 1 H NMR spectral, and elemental analysis. This report represents the first case in which surfactant CTAB has been explored in the synthesis of fused chromenoquinolones in water. A probable reaction mechanism has been established to know the role of CTAB.

Application of Cyclohexane‐1,3‐diones in the Synthesis of Six‐Membered Nitrogen‐Containing Heterocycles

“…The reaction has been carried out by the treatment of 5,5-dimethyl cyclohexane-1,3-dione with 4hydroxy coumarin, substituted amines and aldehydes under ultrasonication. [132] In 2017, a similar reaction reported for chromeno [4,3-b]quinolones synthesis from cyclic-1,3-diketone, 4-hydroxycoumarin, aqueous ammonia and different aldehydes in catalyst-free, refluxed conditions (Scheme 19). [133] Several methods have been applied for the synthesis of 1,4dihydropyridines under different conditions but very little stress has been given on their asymmetric synthesis.…”

“…prepared a library of polycyclic chromenoquinolone 22 compounds in presence of CTAB in water. The reaction has been carried out by the treatment of 5,5‐dimethyl cyclohexane‐1,3‐dione with 4‐hydroxy coumarin, substituted amines and aldehydes under ultrasonication [132] . In 2017, a similar reaction reported for chromeno[4,3‐b]quinolones synthesis from cyclic‐1,3‐diketone, 4‐hydroxycoumarin, aqueous ammonia and different aldehydes in catalyst‐free, refluxed conditions (Scheme 19).…”

Ultrasound assisted synthesis of 5–7 membered heterocyclic rings in organic molecules

“…Kiana et al effectively synthesized γ‐Fe 2 O 3 @Hap‐SO 3 H catalyst using ultrasound and employed it for the synthesis of 2, 3‐dihydroquinazolin‐4‐1 H ‐ones ( 325 ). Products were synthesized using one pot three component reaction of isatoic anhydride ( 322 ), pyrazole carbaldehyde ( 323 ), and primary amines ( 324 ) (Scheme 64) [115].…”

4‐Hydroxycoumarin: A Versatile Substrate for Transition‐metal‐free Multicomponent Synthesis of Bioactive Heterocycles

“…Another achievement for the synthesis of quinoline fused coumarin 106 has been gained by the research group of Bhosle (Scheme 43). [101] This transformation can be carried out via a four‐component reaction of 4‐hydroxycoumarin 1 , dimedone 103 , amine 4 , and aldehydes 37 in an aqueous micellar medium under ultrasound irradiation. By using 20 mol% of surfactant CTAB as the catalyst, the corresponding products 106 were obtained in 72–92% yield.…”