Facile Synthesis of Fully Decorated Imidazo[4,5‐b] and Imidazo[4,5‐c] Pyridines in Aqueous DMF via C‐H Activation under Microwave Irradiation

Avinesh, P.; Jaison, Thadathil. J.; Sajith, Ayyiliath M.; Nagaswarupa, H.P.; Muralidharan, A.

doi:10.1002/slct.201600374

Cited by 9 publications

(2 citation statements)

References 42 publications

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“…The use of a copper catalyst and bathophenanthroline as a ligand were found to be instrumental in driving these reactions to completion. The optimized protocol was further extended to alkyl/aryl/heteroaryl potassium organotrifluoroborates [ 94 ].…”

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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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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“…In 2016, Sajith and co-workers described the direct C-2-H arylation of N-protected imidazo[4, 5-b]pyridines 108 and imidazo[4,5-c]pyridines 110 to furnish compounds 109 and 111, respectively (Scheme 44). 67 For the first time, boronic acids were used as coupling partners. This copper-catalyzed coupling took place in the presence of a ligand, bathophenanthroline (bathophen or BPhen), in a mixture of solvents (DMF/water) and under microwave irradiation.…”

Section: Scheme 43 C-2 Arylation Of Imidazo[45-b]pyridinesmentioning

confidence: 99%

An Update on Direct C–H Bond Functionalization of Nitrogen-Containing Fused Heterocycles

Aziz

Piguel

2017

Synthesis

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This report highlights the recent advances in direct C–H bond functionalization of 5,5- and 6,5-fused heterocycles containing at least two nitrogen atoms. Besides C–C bond formation, C–N, C–S, C–P, and C–Si bonds can also be created via a metal-catalyzed process. Some examples, where a C–H functionalization approach was applied for the synthesis of drug candidates, will be presented as well.1 Introduction2 C–H Functionalization Reactions of N-Containing Heterocycles2.1 Imidazo[1,2-a]pyridines2.2 Pyrrolo[1,2-a]pyrazines2.3 Imidazo[1,2-b]pyrazoles2.4 Imidazo[1,2-a]pyrimidines2.5 Imidazo[1,2-a]pyrazines and Imidazo[1,5-a]pyrazines2.6 Imidazo[1,2-b]pyridazines2.7 Imidazo[4,5-b]pyridines and Imidazo[4,5-c]pyridines2.8 Pyrazolo[3,4-b]pyridines2.9 Pyrazolo[1,5-a]pyrimidines2.10 Pyrrolo[2,3-d]pyrimidines and Pyrrolo[3,2-d]pyrimidines2.11 Imidazo[1,2-b][1,2,4]triazines2.12 Imidazo[1,2-b][1,2,4,5]tetrazines3 Outlook4 Conclusion

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Transition Metal‐Catalyzed C–H Functionalization of Imidazo‐fused Heterocycles

Sakhuja¹,

Kumar²

2023

Transition‐Metal‐Catalyzed C‐H Functionalization of Heterocycles

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Facile Synthesis of Fully Decorated Imidazo[4,5‐b] and Imidazo[4,5‐c] Pyridines in Aqueous DMF via C‐H Activation under Microwave Irradiation

Cited by 9 publications

References 42 publications

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

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

An Update on Direct C–H Bond Functionalization of Nitrogen-Containing Fused Heterocycles

Transition Metal‐Catalyzed C–H Functionalization of Imidazo‐fused Heterocycles

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