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A mechanochemistry-driven practical and efficient synthetic protocol for accessing diverse series of biologically relevant poly-functionalized 5-(arylselanyl)-1H-1,2,3-triazoles through copper(I)-catalyzed click reaction between aryl/heteroaryl acetylenes, diaryl diselenides, benzyl bromides, and sodium azide has been accomplished under high-speed ball-milling. Advantages of this method include operational simplicity, avoidance of using solvent and external heating, one-pot synthesis, short reaction time in minutes, good to excellent yields, broad substrate scope, and gram-scale applications. Furthermore, synthesized organoselenium compounds were synthetically diversified to biologically promising selenones.
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A straightforward and practical method has been developed to access α-substituted glutaric diesters from acrylates and aldehydes using visible light, with Eosin Y facilitating hydrogen atom transfer (HAT) and subsequent Giese-type addition. Also, sunlight has been successfully used as an alternative sustainable light source. The method has also been explored to access substituted 4,5-dihydro-2H-pyridazinones, which have potential biological and industrial applications. Comprehensive mechanistic investigations have been carried out.
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A practical and efficient method for the synthesis of functionalized 4-(aryl-/heteroaryl-ethynyl)chroman-2-ones and 2-(aryl-/heteroaryl-ethynyl)chroman-4-ones through copper-catalyzed decarboxylative direct cross-coupling of coumarin-/chromone-3-carboxylic acids with terminal alkynes, leading to the formation of C(sp)-C(sp3) bonds, has been unearthed. Advantages of this protocol include avoidance of any ligands and bases, a broad substrate scope, tolerance of diverse functional groups, and good to excellent yields.
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Quinoxalinones are a privileged class of compounds, and their structural framework is found in many bioactive compounds, natural compounds, and pharmaceuticals. Quinoxalinone is a promising scaffold for different types of functionalization, and the slight modification of the quinoxalinone skeleton is known to offer a wide range of compounds for drug discovery. Owing to the importance of the quinoxalinone scaffold, we have developed a base-mediated protocol for the C3-alkylation of quinoxalinone followed by tandem cyclization to access novel types of strenuous and fused dihalo-aziridino-quinoxalinone heterocycles via the construction of C-C and C-N bonds. The protocol proved to be simple and practical to access desired fused quinoxalinone heterocycles in excellent yields (up to 98% yield). As an application, the highly functionalized fused dihalo-aziridino-quinoxalinone molecule has been further utilized for mono-dehalogenation under visible light irradiation and selective amide reduction. Moreover, the protocol has also been demonstrated on a gram scale.
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Descoberta de Drogas , Ciclização , AlquilaçãoRESUMO
A one-pot room-temperature-based three-component reaction strategy has been accomplished to access a new series of bio-relevant barbituric/2-thiobarbituric acid hydrazones from the reaction between barbituric/2-thiobarbituric acids, primary aromatic amines, and tert-butyl nitrite in an acetonitrile solvent, without the aid of any catalysts/additives. The ambient reaction conditions can efficiently implement the C(sp3)-H functionalization of barbituric/2-thiobarbituric acids via C-5 dehydrogenative aza-coupling. The process does not require column chromatographic purification; pure products are obtained by simple filtration of the resulting reaction mixture, followed by washing the crude residue with distilled water. The catalyst-free ambient reaction conditions, operational simplicity, broad substrate scope and tolerance for various functional groups, no need for chromatographic purification, good to excellent yields of products within reasonable reaction times in minutes, clean reaction profile, and gram-scale synthetic applicability make this procedure attractive, green, and cost-effective.
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A visible light (white light-emitting diode/direct sunlight)-driven photochemical synthesis of a new series of biologically interesting 3-(alkyl/benzylthio)-4-hydroxy-2H-chromen-2-ones has been achieved through a cross-dehydrogenative C3-H sulfenylation of 4-hydroxycoumarins with thiols at ambient temperature in the presence of rose bengal in acetonitrile under an oxygen atmosphere. The notable features of this newly developed method are mild reaction conditions, energy efficiency, metal-free synthesis, good to excellent yields, use of low-cost materials, and eco-friendliness.
Assuntos
4-Hidroxicumarinas , Rosa Bengala , Luz , Fármacos Fotossensibilizantes , Oxigênio Singlete , Compostos de SulfidrilaRESUMO
A water-mediated and catalyst-free practical method for the synthesis of a new series of pharmaceutically interesting functionalized 5-(2-arylimidazo[1,2-a]pyridin-3-yl)pyrimidine-2,4(1H,3H)-diones has been accomplished based on a one-pot multicomponent reaction between arylglyoxal monohydrates, 2-aminopyridines/2-aminopyrimidine, and barbituric/N,N-dimethylbarbituric acids under reflux conditions. The salient features of this protocol are avoidance of any additive/catalyst and toxic organic solvents, use of water as reaction medium, clean reaction profiles, operational simplicity, ease of product isolation/purification without the aid of tedious column chromatography, good to excellent yields, and high atom-economy and low E-factor.