Synthesis of Substituted Benzimidazoles and Benzoxazoles by Iron‐catalysed Reductive Carbonylation of Aryl Iodides

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(27)

Published: July 16, 2024

Abstract This work describes a novel iron‐catalysed approach for the synthesis of aryl‐substituted benzimidazoles and benzoxazoles. The methodology employs reductive carbonylation using readily available aryl iodides amines as precursors, with carbon monoxide serving efficient carbonyl source. reaction proceeds under mild conditions addition hydrosilanes bases. Notably, aldehydes are generated in situ from iodides, which subsequently react o‐phenylenediamine or 2‐aminophenol to afford desired products high yields. structures synthesized benzoxazoles were confirmed 1 H 13 C NMR spectroscopy mass spectrometry.

Language: Английский

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Metal-free direct annulation of 2-aminophenols and 2-aminothiophenols with unactivated amides through transamidation: Access to polysubstituted benzoxazole and benzothiazole derivatives

Tetrahedron, Journal Year: 2022, Volume and Issue: 115, P. 132794 - 132794

Published: April 28, 2022

Language: Английский

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Palladium‐Catalyzed Dehydrogenative Synthesis of Imidazoquinolines in Water

Asian Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 11(10)

Published: Sept. 19, 2022

Abstract We report a synthesis of imidazoquinolines via dehydrogenative coupling 3,4‐diaminoquinolines with benzylic alcohols utilizing our π‐benzylpalladium(II) system in water. Readily available initially undergo catalytic dehydrogenation to form benzaldehydes, which are then reacted sequential cyclocondensation/aromatization, leading the formation imidazoquinolines. This experimentally simple and practical one‐pot procedure provides direct access desired products without adding strong bases, toxic oxidants or other additives. Several experiments were carried out toward an understanding reaction mechanism propose plausible cycles. The was found be first order respect benzyl alcohol Pd catalyst, zero 3,4‐diaminoquinoline substrate. A kinetic isotope effect 3.1 observed by separately determining rates benzyl‐α,α‐ d 2 alcohol. Water molecules accelerate coupling, suggesting that they act as proton donor activate hydrogen‐bonding network.

Language: Английский

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Construction of Fe3O4@BTH-Pyr-CuCl nanocomposite as a highly active magnetically reusable catalyst for arylation of a category of heterocycles

Research on Chemical Intermediates, Journal Year: 2024, Volume and Issue: 50(5), P. 2131 - 2156

Published: March 14, 2024

Language: Английский

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Step- and atom-economical synthesis of 2-aryl benzimidazoles via the sulfur-mediated redox condensation between o-nitroanilines and aryl methanols

Tetrahedron, Journal Year: 2022, Volume and Issue: 121, P. 132918 - 132918

Published: July 15, 2022

Language: Английский

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