An unprecedented (NH)SO mediated metal-free three-component alkene oxyalkynylation using HO or alcohol as oxygenation agent is described. Mechanistic studies suggested that the reversed regioselectivity should be dictated by an alkene radical cation intermediate.
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http://dx.doi.org/10.1021/acs.orglett.8b02954 | DOI Listing |
A one-pot, acid-, base-, and metal-free, multicomponent strategy has been developed to synthesize spiro thiochromene-oxindole derivatives as potential anti-inflammatory agents. The synthesized compounds were screened for their anti-inflammatory activity by inhibiting heat-induced Bovine Serum Albumin (BSA) denaturation assay, revealing moderate to good efficacy. Compounds 4e, 4k, and 4h exhibited the highest activity, inhibiting BSA denaturation by 90.
View Article and Find Full Text PDFChemistry
December 2024
Technical Institute of Fluorochemistry, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing, 211816, China.
Polyaromatics, as the assembly of diverse cyclic π-systems, exhibit unique physicochemical properties when compared to their individual constituents. In this study, we developed a strategic connection of two azacycles via a furan bridge through a defluorinative diazolation-cyclization reaction of trifluoromethyl enones and N-heterocycles. A range of modular 2,4-furan-bridged triheterocycles (FBTHs), featuring a C3-trifluoromethyl group, was synthesized with broad substrate scope and good regioselectivity under transition metal-free conditions.
View Article and Find Full Text PDFJ Org Chem
January 2025
Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang 414006, P. R. China.
An efficient and facile method has been developed for the construction of novel P-S-C and P-Se-C bonds by facilitating the three-component cross-coupling reaction of P-H bonds with elemental sulfur/selenium and vinylsulfonium salts, utilizing sodium bicarbonate as a base. This approach eliminates the need for the use of toxic and odorous active sulfur/selenium reagents and noble metals, thereby offering a new pathway for synthesizing -phosphinothioates and -phosphinoselenoates via the organic conversion of inorganic sources. The reaction has showcased remarkable versatility in terms of substrate applicability, particularly for organophosphorus compounds containing P-H bonds and vinylsulfonium salt derivatives.
View Article and Find Full Text PDFOrg Biomol Chem
December 2024
School of Safety Science and Engineering, Changzhou University, Changzhou, Jiangsu 213164, China.
A novel three-component radical cyclization/haloazidation of enynones, employing TMSN as the azide source and NIS (NBS or NCS) as the halogen source, has been developed under metal-free conditions for the efficient synthesis of various 1-indanones with moderate yields and acceptable / ratio. The reaction progresses through a sequence involving radical addition, 5- cyclization, and radical coupling, ultimately resulting in the formation of three new chemical bonds and a new ring in a single step. The synthetic benefits of this method have been proven by large-scale experiments and late-stage modification.
View Article and Find Full Text PDFJ Org Chem
December 2024
College of Material, Chemistry and Chemical Engineering, Key Laboratory of Organosilicon Chemistry and Material Technology, Ministry of Education, Hangzhou Normal University, 2318 Yuhangtang Road, Hangzhou 311121, China.
3-Substituted indoles are an important framework of many drugs, agricultural chemicals, functional materials, and bioactive compounds. Malononitrile-based three-component Yonemitsu reactions are attractive choices for the synthesis of 3-substituted indole derivatives but suffered from long reaction time and harsh conditions (e.g.
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