A Zn(OTf)-promoted cyclization reaction of tosylhydrazones with 2-(dimethylamino)malononitrile has been successfully developed providing an efficient strategy for the synthesis of substituted 1-tosyl-1H-pyrazoles.
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Photoinduced synthesis of trisubstituted allylic molecules migratory allylation of olefins.
Chem Commun (Camb)
January 2025
Shanghai Frontiers Science Center for Chinese Medicine Chemical Biology, Institute of Interdisciplinary Integrative Medicine Research, Shanghai University of Traditional Chinese Medicine, No. 1200, Cailun Road, Shanghai 201203, China.
A transition-metal-free method to afford diverse trisubstituted allylic molecules migratory allylation of olefins under light irradiation is described. This system tolerated diverse -tosylhydrazones and olefinic boronic acids. Successful allylation of drugs and natural-product analogues was achieved.
View Article and Find Full Text PDFThree-component diels-alder reaction through palladium carbene migratory insertion enabled dearomative C(sp)-H bond activation.
Nat Commun
December 2024
Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research, Ministry of Education of China, Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province, College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha, Hunan, 410081, China.
Owning to the versatile nature in participation of Diels-Alder (D-A) reactions, the development of efficient approaches to generate active ortho-quinodimethanes (o-QDMs) has gained much attention. However, a catalytic method involving coupling of two readily accessible components to construct o-QDMs is lacking. Herein, we describe a palladium carbene migratory insertion enabled dearomative C(sp)-H activation to form active o-QDM species through the cross-coupling of N-tosylhydrazones with aryl halides.
View Article and Find Full Text PDFUmpolung of -Tosylhydrazones: Synthesis of -Cyano Tosylhydrazones and Their [3,3]-Sigmatropic Rearrangement to 2-Aminoimidazoles.
J Org Chem
December 2024
School of Pharmacy, Lanzhou University, Lanzhou 730000, P. R. China.
The umpolung of -tosylhydrazones was reported for the first time. Synthesis of -cyano tosylhydrazones was developed, and various -cyano tosylhydrazones were prepared in good yields. An umpolung -tosylhydrazones mechanism was proposed.
View Article and Find Full Text PDFPhotochemical carboborylation and three-component difunctionalization of α,β-unsaturated ketones with boronic acids tosylhydrazones.
Chem Sci
November 2024
Departamento de Química Orgánica e Inorgánica, Instituto Universitario de Química Organometálica "Enrique Moles", Instituto de Investigación Sanitaria del Principado de Asturias (ISPA), Centro de Innovación en Química Avanzada (ORFEO-CINQA), Universidad de Oviedo C/ Julián Clavería 8 33006 Oviedo Spain
The reactions of cyclic α,β-unsaturated -tosylhydrazones and alkylboronic acids promoted by 370-390 nm light in the presence of a base give rise to allylic boronic acids that can be trapped as the corresponding pinacolboronates by treatment with pinacol. This reaction features wide scope regarding both coupling partners and functional group tolerance, allowing for the incorporation of a variety of natural product-derived fragments. The allylic boronic acids can be also reacted in a one-pot process with aldehydes, to produce homoallylic alcohols with very high diastereoselectivity.
View Article and Find Full Text PDFPalladium-catalyzed cascade cyclization of α,β-unsaturated -tosylhydrazones with iodoarenes: access to 2-chromenes and 2-quinolines.
Org Biomol Chem
November 2024
College of Chemistry and Chemical Engineering, Nantong University, Nantong 226019, People's Republic of China.
A palladium-catalyzed cascade reaction of α,β-unsaturated -tosylhydrazones with iodoarene derivatives containing a nucleophilic group has been developed, which provides facile access to 2-chromenes and 2-quinolines, respectively. Additionally, the double Pd-carbene migratory insertion/nucleophilic substitution processes for the synthesis of a ternary heterocyclic skeleton were possible in the developed catalytic system.
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