Copper promoted desulfurization and C-N cross coupling reactions: Simple approach to the synthesis of substituted 2-aminobenzoxazoles and 2,5-disubstituted tetrazole amines

Boddapati, S. N. Murthy; Saketi, Jagan Mohana Rao; Mutchu, Baby Ramana; Bollikolla, Hari Babu; Adil, Syed Farooq; Khan, Mujeeb

doi:10.1016/j.arabjc.2019.09.001

Cited by 9 publications

(2 citation statements)

References 87 publications

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“…Based on these experimental investigations and the available literature [37,[40][41][42][43][44][45][46][47][48][49][50], the mechanism for the formation of the final product 2-phenylaminobenzimidazole is very much similar to the mechanism reported for cobalt catalysis [37] (see supporting information Scheme S1).…”

Section: (4) (5)supporting

confidence: 66%

Copper-Promoted One-Pot Approach: Synthesis of Benzimidazoles

et al. 2020

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A facile, one-pot, and proficient method was developed for the production of various 2-arylaminobenzimidazoles. This methodology is based for the first time on a copper catalyst promoted domino C–N cross-coupling reaction for the generation of 2-arylaminobenzimidazoles. Mechanistic investigations revealed that the synthetic pathway involves a copper-based desulphurization/nucleophilic substitution and a subsequent domino intra and intermolecular C–N cross-coupling reactions. Some of the issues typically encountered during the synthesis of 2-arylaminobezimidazoles, including the use of expensive catalytic systems and the low reactivity of bromo precursors, were addressed using this newly developed copper-catalyzed method. The reaction procedure is simple, generally with excellent substrate tolerance, and provides good to high yields of the desired products.

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Section: (4) (5)supporting

confidence: 66%

Copper-Promoted One-Pot Approach: Synthesis of Benzimidazoles

et al. 2020

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“…Tetrazoles as nitrogen rich structures of organic compounds were employed in pharmaceuticals, medicine, biochemistry, photographic agents and especially in explosives. [44][45][46] Moreover, tetrazoles serve in coordination chemistry and have also been applied in several useful biochemical transformations. [47][48][49] In addition, tetrazoles can be used as stable replacements for carboxylic acid groups in drug design.…”

Section: Introductionmentioning

confidence: 99%

Guanidine complex of copper supported on boehmite nanoparticles as practical, recyclable, chemo and homoselective organic–inorganic hybrid nanocatalyst for organic reactions

Jafari

Ghorbani‐Choghamarani

Hasanzadeh

2020

Applied Organom Chemis

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Boehmite (BO) nanoparticles (NPs) were prepared via the injection of aqueous NaOH solution to aqueous aluminum nitrate solution at room temperature. Afterwards, a new complex of copper was immobilized on BO-NPs (Cu-Guanidine@BO-NPs). This heterogeneous nanocatalyst was used as a practical, recyclable, chemo and homoselective nanocatalyst in the organic processes, i.e. the preparation of tetrazole five-membered heterocycles and chemoselective sulfoxidation of sulfides using H 2 O 2 as oxidant. In this sense, the prepared nanocatalyst was characterized by AAS, N 2 adsorptiondesorption isotherms, WDX, EDS, SEM, and TGA techniques. The reusability of this catalyst was investigated in the described organic reactions for several runs without notable loss of its catalytic activity. Moreover, all of the tetrazole and sulfoxide derivatives were isolated in high Turn Over Number (TON) and Turn Over Frequency (TOF) numbers indicating the high activity and selectivity of Cu-Guanidine@BO-NPs in the described reactions.

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Iron‐Promoted Redox Access to 2‐Aminobenzoxazoles from Amines, Carbon Disulfide and 2‐Nitrophenols

Long Le,

Yen Tran,

Anh Nguyen

et al. 2024

Asian J Org Chem

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A method to assemble 2‐aminobenzoxazoles via iron‐catalyzed redox condensation of amines, carbon disulfide and 2‐nitrophenols is reported. The reaction features advantages of environmentally friendly iron catalyzed conditions, readily available starting materials, and excellent atom‐, step‐ and redox economy compared to known protocols. Experimental investigation suggests a mechanism encompassing iron‐catalyzed reduction of the nitro group of 2‐nitrophenols by the dithiocarbamate group from amine‐CS2 adduct.

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Copper promoted desulfurization and C-N cross coupling reactions: Simple approach to the synthesis of substituted 2-aminobenzoxazoles and 2,5-disubstituted tetrazole amines

Cited by 9 publications

References 87 publications

Copper-Promoted One-Pot Approach: Synthesis of Benzimidazoles

Copper-Promoted One-Pot Approach: Synthesis of Benzimidazoles

Guanidine complex of copper supported on boehmite nanoparticles as practical, recyclable, chemo and homoselective organic–inorganic hybrid nanocatalyst for organic reactions

Iron‐Promoted Redox Access to 2‐Aminobenzoxazoles from Amines, Carbon Disulfide and 2‐Nitrophenols

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