An acid-catalyzed multicomponent tandem double cyclization protocol has been developed for the synthesis of polyfunctional 4,9-dihydropyrrolo[2,1-b]quinazolines from simple and readily available arylglyoxal monohydrates, 2-aminobenzylamine, and trans-β-nitrostyrenes. This practical and metal-free reaction proceeds through an imine formation/cyclization/Michael addition/Henry cyclization protocol, resulting in the construction of four new bonds and two ring moieties directly in one pot.
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http://dx.doi.org/10.1021/acs.joc.6b01660 | DOI Listing |
Org Biomol Chem
January 2025
Jiangxi Provincial Key Laboratory of Functional Crystalline Materials Chemistry, Jiangxi University of Science and Technology, Ganzhou 341000, Jiangxi Province, P.R. China.
The multi-component ring-opening reactions of cyclic ethers offer an efficient strategy for the rapid introduction of multiple functional groups and the construction of complex molecular architectures. Despite the minimal ring strain in five- and six-membered rings presenting a significant challenge for ring-opening, advancements have been made. Traditional acid-catalyzed pathways have been complemented by a novel approach involving carbene-induced oxonium intermediate formation, which has emerged in recent years and expanded the selectivity of ring-opening reactions.
View Article and Find Full Text PDFFront Chem
October 2024
Bio-Organic Division, Bhabha Atomic Research Centre, Mumbai, India.
With the aim to develop a FRET-based viscosity sensor, two dyad molecules, and , comprising tetraarylpyrrolo[3,2-]pyrrole (TAPP) (donor) and naked boron-dipyrromethene (BODIPY) dyes (acceptor), were designed. Dyads were synthesized via acid-catalyzed multicomponent reactions followed by Sonogashira coupling. In both dyads, the BODIPY and TAPP moieties are linked through phenylethynyl groups, which allow free rotation of the BODIPY dyes; that is, they can act as molecular rotors.
View Article and Find Full Text PDFChemistry
August 2024
State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, 163 Xianlin Avenue, 210023, Nanjing, Jiangsu, China.
ACS Omega
January 2024
Molecular Design and Synthesis, Department of Chemistry, KU Leuven, Leuven 3000, Belgium.
In this study, a homogeneous acid-catalyzed reaction of a series of benzaldehydes, benzylamines, and Meldrum's acid was presented, allowing the novel one-pot and multicomponent synthesis of hexahydroquinolines with high stereoselectivity. The current strategy has advantages including high regioselectivity, good efficiency, reasonable diversity, utilization of an inexpensive and safe catalyst, and easy purification of products by simple recrystallization. The current reaction utilizes 2 equiv of Meldrum's acid, 3 equiv of benzaldehyde derivatives, and one equiv of amine derivatives to yield (4'S,5'S,7'S)-1'-benzyl-2,2-dimethyl-4',5',7'-triphenyl-3',4',7',8'-tetrahydro-1'-spiro[[1,3]dioxane-5,6'-quinoline]-2',4,6(5')-trione derivatives.
View Article and Find Full Text PDFMol Divers
October 2024
Department of Chemistry, Deogiri College, Aurangabad, Maharashtra, 431005, India.
Pyranopyrazoles are among the most distinguished, biologically potent, and exciting scaffolds in medicinal chemistry and drug discovery. Synthesis and design of pyranopyrazoles using functional modifications via multicomponent reactions (MCRs) are thoroughly found in synthetic protocols by forming new C-C, C-N, and C-O bonds. This review aims to focus on the biological importance of pyranopyrazoles as well as on a diverse synthetic approach for their synthesis using various catalytic systems such as acid-catalyzed, base-catalyzed, ionic liquids and green media-catalyzed, nano-particle-catalyzed, metal oxide-supported catalysts, and silica-supported catalysts.
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