Copper catalyzed tandem oxidative C–H amination/cyclizations: Direct access to imidazo[1,2-a]pyridines

Pericherla, Kasiviswanadharaju; Kaswan, Pinku; Khedar, Poonam; Khungar, Bharti; Parang, Keykavous; Kumar, Anil

doi:10.1039/c3ra43889a

Cited by 66 publications

(21 citation statements)

References 58 publications

(50 reference statements)

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“…In addition, they further developed a one-pot synthesis of imidazo[1,2-a]pyridines 1.97b through multicomponent couplings of 2-aminopyridines, aldehydes and arylalkynecarboxylic acids 1.96b, which were generated in situ through palladium-catalyzed coupling of aryl iodides and propiolic acid (Scheme 25) [65]. Pericherla et al [73] have developed a simple and convenient strategy for the synthesis of imidazo[1,2-a]pyridines via inexpensive copper catalyzed tandem imine formation and intramolecular aerobic oxidative C-H bond amination/cyclizations (Scheme 33). A series of imidazo[1,2-a]pyridines were synthesized by the reaction of readily ten available acetophenones and 2-aminopyridines in good to excellent yields (48-92 %).…”

Section: Reaction Of 2-aminopyridines With Nitroalkenesmentioning

confidence: 99%

Recent synthetic scenario on imidazo[1,2-a]pyridines chemical intermediate

2015

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Of the biologically important benzene fused heterocycles, the most important are those containing a ring-junction nitrogen. The majority of ring junction systems do not occur naturally, but they have been important from a theoretical viewpoint, for preparation of potentially active analogues. The imidazo[1,2-a] pyridines are an important class of nitrogen ring junction heterocyclic compounds. They have huge applications in medicinal chemistry and drug molecule production. Thus, the initial discussion focuses on synthetic strategies of imidazo[1,2-a] pyridines, and later we disclose the reactivity of the imidazo[1,2-a]pyridines. This review is intended to summarize and discuss the most recent developments of synthesis and reactivity of imidazo[1,2-a]pyridines, mainly the contributions after 2007.

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Section: Reaction Of 2-aminopyridines With Nitroalkenesmentioning

confidence: 99%

Recent synthetic scenario on imidazo[1,2-a]pyridines chemical intermediate

2015

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“…The Schlenk tube was quickly evacuated, closed under vacuum, and then refilled with oxygen using an oxygen balloon. The resulting mixture was stirred at 40 °C for 24 h. After the completion of reaction, the residue was directly purified by flash column chromatography using ethyl acetate and petroleum ether as eluents to afford the pure product [ 32 ].…”

Section: Experiments Sectionsmentioning

confidence: 99%

Synthesis and Biological Evaluation of Novel Benzimidazole Derivatives and Analogs Targeting the NLRP3 Inflammasome

et al. 2017

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A series of benzo[d]imidazole analogues of thiabenzole were synthesized and their anti-inflammatory activities toward NLRP3 (nucleotide-binding domain leucine-rich repeat containing protein family, pyrin domain-containing 3, also known as cryopyrin or NALP3) inflammasome were evaluated in vitro. Two lead compounds, TBZ-09 and TBZ-21, were identified by anti-production of IL-1β. In the second round of biological evaluation, based on the lead, 34 more compounds were synthesized and their in vitro anti-inflammatory activities were investigated. Several compounds were identified as anti-inflammatory agents that can reduce IL-1β expression in a dose-dependent manner. A preliminary structure–activity relationship is also summarized here.

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“…In(OTf ) 3 could be used as Lewis acids to accelerate the -iodination step of this transformation [105]. Recently, Kumar et al reported a CuI-catalyzed synthesis of imidazo[1,2-a]pyridines in dioxane without ligand and additive [106].…”

Section: Five-membered-ring Formation 259mentioning

confidence: 99%