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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.
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http://dx.doi.org/10.1021/acs.orglett.4c04097 | DOI Listing |
Org Biomol Chem
August 2025
School of Chemistry, College of Science, University of Tehran, 14155-6455 Tehran, Iran.
We report the simple synthesis of 1,2-disubstituted benzimidazoles using three versatile building blocks: benzaldehydes, -phenylenediamines, and phenylpropiolic acid. The protocol facilitates the formation of three C-N bonds and one Csp-Csp bond in a one-pot reaction and yields novel products that have not been previously synthesized.
View Article and Find Full Text PDFInt J Mol Sci
July 2025
School of Chemical & Environmental Engineering, Pingdingshan University, Pingdingshan 467000, China.
Our work introduces a facile and efficient metal-free [3+3] annulation approach for the synthesis of polysubstituted pyridines via the reaction between β-enaminonitriles and β,β-dichloromethyl peroxides. This strategy operates under mild conditions, demonstrating broad substrate scope and excellent functional group tolerance. Mechanistic investigations suggest that the reaction proceeds through a Kornblum-De La Mare rearrangement followed by SV-type C-Cl bond cleavage and intramolecular cyclization/condensation.
View Article and Find Full Text PDFNat Commun
August 2025
Institute of Organic Chemistry, RWTH Aachen University, Aachen, Germany.
Phenols and their derivatives are highly relevant motifs in pharmaceuticals, natural products, and other functional materials. Conventional strategies for phenol synthesis rely on classical aromatic functionalization, which is often dictated by electronic and steric factors. Herein, we report an alternative approach for phenol synthesis where irradiation in the presence of Lewis or Brønsted acids enables the selective migration of alkyl and aryl groups from meta to either the ortho or para positions.
View Article and Find Full Text PDFChem Biodivers
August 2025
Department of Chemistry, Faculty of Science, Sohag University, Sohag, Egypt.
The exponential rise in resistance to pesticides and conventional antibiotics is another important factor propelling the development of novel medicines and substances with insecticidal efficacy. One approach to this experiment is to look at novel families of insecticidal compounds with different mechanisms of action. Consequently, a one-pot four-component synthesis involving benzil, aryl carbaldehydes, CHCOONH and N,N-dimethylpropane-1,3-diamine, and/or 1-aminopropan-2-ol was used to successfully synthesize polysubstituted imidazoles 5a-5j.
View Article and Find Full Text PDFCurr Top Med Chem
August 2025
School of International Studies, Harbin Institute of Technology, No. 92 Xidazhi Street, Nangang District, Harbin, 150001, P.R. China.
Pyridine alkaloids possess important biological activities and are widely used in fields such as medicine and pesticides. This paper comprehensively reviews the research progress in the chemical synthesis and biosynthesis of pyridine alkaloids. In terms of chemical synthesis, there are diverse synthesis methods for arylpyridine compounds.
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