Preparation of 2‐Azido‐1‐Substituted‐1 <i>H</i>‐Benzo[<i>d</i>]imidazoles Using a Copper‐Promoted Three‐Component Reaction and Their Further Conversion into 2‐Amino and 2‐Triazolyl Derivatives

Tamminana, Ramana; Punniyamurthy, Tharmalingam

doi:10.1002/chem.201202215

Cited by 52 publications

(15 citation statements)

References 66 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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“…Cobalt can co‐ordinate with thiourea and followed by removal of protons to afford intermediate R via intermediates P and Q . The intermediate R may react with 2‐iodoaniline to provide 2‐iodophenyl guanidine A along with by‐products CoS and poly sulphide via desulphurization/substitution . Oxidative addition of A with cobalt complex can lead to the formation of a which can undergo intramolecular C‐N cyclised product B using base via intermediate b .…”

Section: Figurementioning

confidence: 99%

Synthesis of Benzimidazoles via Domino Intra and Intermolecular C‐N Cross‐Coupling Reaction

2018

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The synthesis of aminobenzimidazoles has been demonstrated under mild reaction conditions using cobalt catalyst in one pot reaction. This methodology involved domino intra and intermolecular C-N cross-coupling reaction. In addition, functional group tolerance has been also explored.Benzimidazoles [1][2][3][4][5][6][7][8][9][10] and 2-aminobenzimidazoles [11][12][13][14][15][16][17][18][19][20][21] are very powerful compounds because of their applications in therapeutic [22][23] and biological sciences ( Figure 1). [24][25] These compounds were used as neuropeptide YY1 receptor antagonist, [26] N-methyl-D-aspartate (NMDA) antagonist, [27] factor Xa(FXa) inhibitor, [28] poly(ADP-ribose)polymerase (PARP) inhibitor [29] and non-peptide thrombin inhibitor. [30] In addition, these compounds show anti-inflammatory, antimicrobial and antibacterial activities. [31] Apart from that, these compounds can also be used for the synthesis of dyes and high-temperature resistance polymers. [32] Therefore, the construction of benzimidazole derivatives were developed by many researchers via both traditional methods [33][34][35] and C-N cross-coupling reactions using various transition metals such as Cu, [36][37][38][39][40] Pd, [41][42][43] Co, [44] Zn, [45][46][47] and Ru. [48] In this connection, we would like to demonstrate the methodology for the synthesis of benzimidazoles from thiourea in one pot reaction via desulphurization/substitution/domino C-N cross-coupling reaction using cobalt source as catalyst under mild reaction conditions.

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“…It reacts with amines to form substituted thioureas ( 1 a‐1 l ). Then, copper (I) species (could be formed from Cu(II) salt) co‐ordinates to sulfur in thiourea followed by desulphurization (CuS was formed as byproduct and an extra sulphur might have converted into as polysulfide)– and nucleophilic substitution with NaN 3 to afford the intermediate C via intermediates A and B . Electrocyclization of C afforded the target products 2 a–2 l .…”

Section: Figurementioning

confidence: 99%

Efficient Copper‐Promoted Tandem Multi‐Component Strategy: The Synthesis of 1‐ Aryl/Alkyl‐5‐(N‐Benzoylamino) Tetrazoles and Guanidine's

Shaik¹,

Seelam²,

Tamminana

et al. 2017

ChemistrySelect

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Efficient, simple and multi component methodology has been demonstrated for the construction of l‐Aryl/Alkyl‐5‐(N‐Benzoylamino) tetrazoles and guanidine's. These compounds can be used as intermediates for the synthesis of heterocyclic compounds such as substituted 2‐(N‐benzoyl) benzimidazoles and fused cyclic tetrazoles. Target products were obtained from benzyol chloride via in situ consecutive formation of benzoyl isothiocyanates and benzyol aryl thiourea. Moreover, desulphurization was also observed during this methodology. In addition, functional group tolerance and reaction mechanism have also been studied.

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Preparation of 2‐Azido‐1‐Substituted‐1 H‐Benzo[d]imidazoles Using a Copper‐Promoted Three‐Component Reaction and Their Further Conversion into 2‐Amino and 2‐Triazolyl Derivatives

Cited by 52 publications

References 66 publications

Copper-Promoted One-Pot Approach: Synthesis of Benzimidazoles

Copper-Promoted One-Pot Approach: Synthesis of Benzimidazoles

Synthesis of Benzimidazoles via Domino Intra and Intermolecular C‐N Cross‐Coupling Reaction

Efficient Copper‐Promoted Tandem Multi‐Component Strategy: The Synthesis of 1‐ Aryl/Alkyl‐5‐(N‐Benzoylamino) Tetrazoles and Guanidine's

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