Trimethylglycine-Betaine-Based-Catalyst-Promoted Novel and Ecocompatible Pseudo-Four-Component Reaction for Regioselective Synthesis of Functionalized 6,8-Dihydro-1′H,5H-spiro[[1,3]dioxolo[4,5-g]quinoline-7,5′-pyrimidine]-2′,4′,6′(3′H)-trione Derivatives

Abstract

Nowadays, synthesis of novel nitrogen-bearing heterocyclic scaffolds is a challenging and also demanding task. In our present work, we demonstrate a novel one-pot pseudofour-component reaction of 3,4-methylenedioxyaniline, N,Ndimethylbarbituric acid, and aryl/heteroaryl aldehydes for the regioselective construction of functionalized 6,8-dihydro-1′H,5H-spiro [[1,3]dioxolo[4,5-g]quinoline-7,5′-pyrimidine]-2′,4′,6′(3′H)-trione scaffolds using a trimethylglycine-betainebased sustainable catalyst. The title derivatives are achieved through the formation of three new C−C bonds and one C− N bond, and two asymmetric carbon centers are generated in the final motif. The present protocol works efficiently, tolerates different substituents present in reactants, has a simple operational procedure, provides excellent reaction yield in a short time, uses a recyclable catalyst, and results in up to 99.7% purity (HPLC) for the synthesized compounds, with high diastereoselectivity (d.r. > 50:1 (syn/anti)), excellent atom economy, reaction mass efficiency, and effective mass yield.

Ionic liquid catalyzed one‐pot multi‐component synthesis of fused pyridine derivatives: A strategy for green and sustainable chemistry

“…As far as environmental sustainability is a concern, it is necessary to validate the present protocol with wellestablished "Green metrics" such as E-factor, Atom economy, Reaction mass efficiency, Effective mass yield, and Optimum efficiency. [38,39] The E-factor is a widely used green metric for the chemical reactions. The lower the value of the E-factor, the more eco-compatible reaction is.…”

Chemical Insights Into the Synthetic Chemistry of Quinazolines: Recent Advances

“…This aerobic oxidative procedure offers a valuable utilization of simple alkyl azide derivatives 111 in N -heterocycle synthesis with nitrogen and water as co-products ( Scheme 27C ). High atom efficiency and good functional group tolerance make this procedure suitable in accessing numerous functionalized quinazolines (Patel and Patel, 2019 ).…”

“…Fluorescence investigation suggested that the synthesized quinazolines exhibit potent fluorescence properties with high quantum yield. These quinazolines have been proposed to be employed as a high fluorescent probe (Patel and Patel, 2019). Parua et al developed nickel [Ni(MeTAA)]-catalyzed approach for the formation of quinazoline derivatives 126 from acceptor-less dehydrogenative coupling of 2-aminobenzylamines 22 with benzyl alcohols 125 and 2-aminobenzylalcohols 88 with benzonitriles 127 in the presence of potassium tertbutoxide in xylene at 100 • C for 24 h (Parua et al, 2018).…”

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)

“…[7][8][9][10] 1,4-Dihydropyridines (as nitrogen-containing heterocycles) with a structure analogous to nicotinamide adenine dinucleotide (NAD) coenzyme have attracted considerable interest due to their different biological and medicinal applications. [7,[11][12][13][14][15][16][17][18][19][20][21] They have increasingly-popular worldwide applications such as antitumor, antisclerotic, antidiabetic, calcium channel blockers, anti-inflammatory, and analgesic. [22] Literature studies clearly show that they also have anti-TB activity owing to their lipophilic groups and can be used in tumor and Alzheimer's disease therapy as well.…”

“…1,4‐Dihydropyridines (as nitrogen‐containing heterocycles) with a structure analogous to nicotinamide adenine dinucleotide (NAD) coenzyme have attracted considerable interest due to their different biological and medicinal applications [7,11–21] . They have increasingly‐popular worldwide applications such as antitumor, antisclerotic, antidiabetic, calcium channel blockers, anti‐inflammatory, and analgesic [22] .…”