Lithium bromide catalyzed solvent free method for synthesis of 2-substituted benzimidazoles and imidazopyridines

Dekhane, Deepak V.; Pawar, Shivaji S.; Gupta, Sunil; Shingare, Murlidhar S.; Thore, Shivaji N.

doi:10.1016/j.cclet.2009.11.034

Cited by 11 publications

(4 citation statements)

References 41 publications

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“…The reaction of 2,3-diaminopyridine 7 with substituted aryl aldehydes in water under thermal conditions (→ 14) [18]. As another alternative, Dekhane et al have successfully mediated solvent free condensation of diaminoaromatic reagents and esters to obtain 2-substituted imidazopyridines 15 in the presence of n-butyl lithium in good to excellent yields at 110-115 °C [19].…”

Section: Synthetic Routes Towards Imidazo[45b]pyridinesmentioning

confidence: 99%

Imidazo[4,5-b]Pyridines: From Kinase Inhibitors to more Diversified Biological Properties

Ferrières

Jarmoni

Misbahi

2024

CMC

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Imidazo[4,5-b]pyridines are amongst the oldest known heteroaromatic derivatives. Their structural similarity with purine basis has however aroused the curiosity of biologists and resulted in the developments of innovative bioactive compounds. This review thus firstly describes the main synthetic ways currently used to produce imidazo[4,5-b]pyridine derivatives, and secondly gives examples of their potential, especially focusing on protein inhibition abilities, thus opening the way to applications as anti-- cancer or antimicrobial agents.

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Section: Synthetic Routes Towards Imidazo[45b]pyridinesmentioning

confidence: 99%

Imidazo[4,5-b]Pyridines: From Kinase Inhibitors to more Diversified Biological Properties

Ferrières

Jarmoni

Misbahi

2024

CMC

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“…The data agreed with that previously reported for compound 10. 30,31 Scheme 2. Synthesis of 2-(3H-imidazo [4,5-b]pyrid-2-yl)acetonitrile 10.…”

Section: Synthesismentioning

confidence: 99%

Synthesis and DTF studies of novel aminoimidazodipyridines using 2-(3H-imidazo[4,5-b]pyridin-2-yl)acetonitrile as an efficient key precursor

Darweesh¹,

El-Fatah²,

Abdel‐Latif³

et al. 2021

Arkivoc

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Novel 9-aminoimidazo[1,2-a:5,4-b']dipyridine-6,8-dicarbonitriles were prepared via the Michael addition reaction of readily accessible 2-(3H-imidazo[4,5-b]pyrid-2-yl)acetonitrile with arylidenemalononitriles. The regioselectivity of the reaction was supported by theoretical calculations at the DFT level. In contrast, the reaction of the appropriate bis-arylidenemalononitrile with 2-(3H-imidazo[4,5-b]pyrid-2-yl)acetonitrile under similar reaction conditions gave the corresponding bis[2-(3H-imidazo[4,5-b]pyrid-2-yl)acrylonitriles].

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“…According to the classical method of benzimidazole synthesis, Dymińska et al proposed the synthesis of imidazo[4,5- b ]pyridine 38 from 2,3-diaminopyridine and formic acid ( Scheme 1 ) [ 75 ]. The first successful lithium bromide mediated solvent free condensation of arylenediamine and esters to obtain 2-substituted imidazopyridines (e.g., 39 ) in good to excellent yields at 110–115 °C was described by Dekhane et al [ 76 ]. Mladenova performed the reaction of methyl 4-((benzyloxy)methyl)tetrahydrofuran-2-carbimidate hydrochloride– cis or trans with 2,3-diaminopyridine in MeOH resulting in the corresponding 1 H -imidazo[4,5- b ]pyridine 40 , cis or trans in a yield of 40% [ 77 ].…”

Section: Synthetic Routes To Imidazo[45- B ]Pymentioning

confidence: 99%

Pharmacological Potential and Synthetic Approaches of Imidazo[4,5-b]pyridine and Imidazo[4,5-c]pyridine Derivatives

2017

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The structural resemblance between the fused imidazopyridine heterocyclic ring system and purines has prompted biological investigations to assess their potential therapeutic significance. They are known to play a crucial role in numerous disease conditions. The discovery of their first bioactivity as GABAA receptor positive allosteric modulators divulged their medicinal potential. Proton pump inhibitors, aromatase inhibitors, and NSAIDs were also found in this chemical group. Imidazopyridines have the ability to influence many cellular pathways necessary for the proper functioning of cancerous cells, pathogens, components of the immune system, enzymes involved in carbohydrate metabolism, etc. The collective results of biochemical and biophysical properties foregrounded their medicinal significance in central nervous system, digestive system, cancer, inflammation, etc. In recent years, new preparative methods for the synthesis of imidazopyridines using various catalysts have been described. The present manuscript to the best of our knowledge is the complete compilation on the synthesis and medicinal aspects of imidazo[4,5-b]pyridines and imidazo[4,5-c]pyridines reported from the year 2000 to date, including structure–activity relationships.

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Lithium bromide catalyzed solvent free method for synthesis of 2-substituted benzimidazoles and imidazopyridines

Cited by 11 publications

References 41 publications

Imidazo[4,5-b]Pyridines: From Kinase Inhibitors to more Diversified Biological Properties

Imidazo[4,5-b]Pyridines: From Kinase Inhibitors to more Diversified Biological Properties

Synthesis and DTF studies of novel aminoimidazodipyridines using 2-(3H-imidazo[4,5-b]pyridin-2-yl)acetonitrile as an efficient key precursor

Pharmacological Potential and Synthetic Approaches of Imidazo[4,5-b]pyridine and Imidazo[4,5-c]pyridine Derivatives

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