An exceptional oxone mediated tandem transformation of 2-aminobenzylamines to 2-substituted benzimidazoles is reported. It occurs at room temperature with aromatic, heteroaromatic, and aliphatic aldehydes. In this reaction initial condensation of 2-aminobenzylamine with appropriate aldehydes afforded a tetrahydroquinazoline intermediate which underwent oxone-mediated ring distortion to afford the desired compounds in moderate to excellent yields. © 2016 American Chemical Society.

Parthapratim Munshi

Chemistry

(SoNS) School of Natural Sciences

Subhabrata Sen

Hati S.

Kumar Dutta P.

Dutta S.

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Shiv Nadar University

Organic Letters

Antimicrobial drug resistance is one of the most critical problems that plagued the human race in modern times. Discovery of novel antibiotics is important to counter this threat. Accordingly, herein we have reported the discovery of substituted benzimidazole class of molecules with antimicrobial property (specifically against Staphylococcus aureus). They were initially identified through a random screening and a novel catalytic synthetic strategy was utilized to access them. in vitro screening and phenotypic profiling revealed the antimicrobial nature. De novo transcriptome and gene analyses predicted the putative targets. This work provides a solid foundation for developing the benzimidazoles as a target specific antimicrobial preclinical candidate. © 2019 Wiley Periodicals, Inc.

Drug Development Research

Transcriptome analysis predicts mode of action of benzimidazole molecules against Staphylococcus aureus UAMS-1

Catalytic cerium chloride was found to activate 2-iodoxybenzoic acid (IBX) for the oxidative dehydrogenation of tetrahydroisoquinolines, tetrahydro-β-carbolines, and thiazolidines to their dehydrogenated and aromatic forms at room temperature in moderate to excellent yields. The robustness of the protocol was demonstrated by scaling up the reactions to multigram quantities. © 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

European Journal of Organic Chemistry

Cerium Chloride Catalyzed, 2-Iodoxybenzoic Acid Mediated Oxidative Dehydrogenation of Multiple Heterocycles at Room Temperature

Nitrogen heteroarenes form an important class of compounds which can be found in natural products, synthetic drugs, building blocks etc. Among the diverse strategies that were developed for the synthesis of nitrogen heterocycles, oxidative dehydrogenation is extremely effective. This review discusses various oxidative dehydrogenation strategies of C-C and C-N bonds to generate nitrogen heteroarenes from their corresponding heterocyclic substrates. The strategies are categorized under stoichiometric and catalytic usage of reagents that facilitate such transformations. The application of these strategies in the synthesis of nitrogen heteroarene natural products and synthetic drug intermediates are also discussed. We hope this review will arouse sufficient interest among the scientific community to further advance the application of oxidative dehydrogenation in the synthesis of nitrogen heteroarenes. © 2017 Hati et al.; Licensee Beilstein-Institut.

Fulltext

Beilstein Journal of Organic Chemistry

Oxidative dehydrogenation of C-C and C-N bonds: A convenient approach to access diverse (dihydro)heteroaromatic compounds

We have demonstrated a facile synthesis of diversely substituted quinazolines and 3,4-dihydroquinazolines through the o-iodoxybenzoic acid (IBX) mediated tandem reaction of readily available o-aminobenzylamine and aldehydes. The yield of the reactions generally ranged from 70\% to 95\%. This mild protocol provides an efficient strategy toward the synthesis of these classes of heterocycles. © Georg Thieme Verlag Stuttgart.

Synthesis (Germany)

Synthesis of Quinazolines and Dihydroquinazolines: o-Iodoxybenzoic Acid Mediated Tandem Reaction of o-Aminobenzylamine with Aldehydes

The Journal of Organic Chemistry

Copper(I)-Catalyzed Regioselective Amination of N-Aryl Imines Using TMSN3 and TBHP: A Route to Substituted Benzimidazoles

Organocatalytic Syntheses of Benzoxazoles and Benzothiazoles using Aryl Iodide and Oxone via C–H Functionalization and C–O/S Bond Formation

Angewandte Chemie International Edition

Cascade Palladium Catalysis: A Predictable and Selectable Regiocontrolled Synthesis ofN-Arylbenzimidazoles

Oxone-Mediated Oxidative Cleavage of β-Keto Esters and 1,3-Diketones to α-Keto Esters and 1,2-Diketones in Aqueous Medium

Accessing Benzimidazoles via a Ring Distortion Strategy: An Oxone Mediated Tandem Reaction of 2-Aminobenzylamines