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Synthesis of Polysubstituted Benzo[][1,5]naphthyridine via Mn(III)-Mediated Domino Cascade Reactions of Cyclopropanols and 2-(2-Isocyanophenyl)acetonitriles.
Org Lett
January 2025
Institute of Next Generation Matter Transformation, College of Material Sciences Engineering at Huaqiao University, 668 Jimei Boulevard, Xiamen, Fujian 361021, China.
Domino cascade reactions, which can construct multiple bonds in one pot, are efficient methods to synthesize N-heterocycles and other useful skeletons. Herein, we report an expedient synthesis of polysubstituted benzo[][1,5]naphthyridine via Mn(III)-mediated C-C bond cleavage of cyclopropanols. These reactions were initiated by addition of β-carbonyl radicals, generated from cyclopropyl alcohols in the presence of Mn(III), to 2-(2-isocyanophenyl)acetonitriles to give quinolin-3-amines, which went through intramolecular cyclizations and dehydrogenation to give the final products.
View Article and Find Full Text PDFRoom-temperature synthesis of FeO@MOF-5 magnetic hybrid as an efficient catalyst for the one-pot green synthesis of tetrahydropyridines.
Sci Rep
December 2024
Department of Organic Chemistry, Faculty of Chemistry and Petroleum Sciences, Bu-Ali Sina University, Hamedan, Iran.
In recent two decades, considerable efforts have been devoted to the room-temperature green syntheses of metal-organic frameworks (MOFs) to reduce energy consumption and increase safety. It could improve some properties (e.g.
View Article and Find Full Text PDFElectrochemical Synthesis of 3-(Sulfonyl)quinol-4-ones from -Alkynyl--(formyl)anilides and Sulfinates.
Org Lett
December 2024
Organic Chemistry Department, Science Faculty, Patrice Lumumba Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklaya strasse, 6, 117198 Moscow, Russia.
Electrolysis of -alkynyl--(formyl)anilides and sodium sulfinates on graphite electrodes delivers biologically sound 3-(sulfonyl)quinol-4-ones with moderate to good yields. The reaction is carried out in an undivided cell in the presence of silver(I) oxide with potassium iodide or sodium tetrafluoroborate as the supporting electrolyte. The reaction tolerates variously substituted anilides as well as aryl and alkyl sulfinates.
View Article and Find Full Text PDFTotal synthesis of the taraxacine A natural product Ag(I)-catalysed imidate-alkyne cyclization.
Org Biomol Chem
December 2024
Organic Chemistry Department, Science Faculty, Patrice Lumumba Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklaya st., 6, 117198 Moscow, Russia.
A domino approach towards β-carboline natural product taraxacine A and its analogues was developed. The main step relies on a silver(I) and base co-catalysed imidate-alkyne cyclization. The reaction tolerates primary and secondary alcohols, and various substitutions in the indole are possible.
View Article and Find Full Text PDFMetal-Free Synthesis of Functionalized Indolizines via a Cascade Michael/S2/Aromatization Reaction of 2-Alkylazaarene Derivatives with Bromonitroolefins.
ACS Omega
December 2024
School of Pharmacy, Guizhou Provincial Engineering Technology Research Center for Chemical Drug R&D, Guizhou Medical University, Guiyang 550014, P. R. China.
A transition metal-free domino Michael/S2/aromatization annulation of 2-pyridylacetates with bromonitroolefins has been developed. A wide range of substrates containing various substituted groups was compatible with the present methodology and afforded functionalized indolizines with moderate to excellent yield (up to 99% yield). In addition, the potential practicality of the method stood out through scale-up reactions and further transformations to other valuable compounds.
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