Iron(III)‐Catalyzed Denitration Reaction: One‐Pot Three‐Component Synthesis of Imidazo[1,2‐<i>a</i>]pyridine Derivatives

Hao, Yan; Wang, Yuling; Pan, Congming; Zhang, Hao; Yang, Shaohua; Ren, Xiaoyu; Li, Jian; Huang, Guosheng

doi:10.1002/ejoc.201301658

Cited by 64 publications

(21 citation statements)

References 53 publications

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“…In addition, by means of scaffold hopping, we devised and synthesized several compounds, which are listed in Figure 2 as benzimidazole mimics. We either replaced carbon atom by nitrogen in the benzimidazole core, AI-26 , AI-27 , AI-28 , AI-31 , AI-32 , and AI-33 , or enlarge the ring of former imidazole part, AI-29 and AI-30 [ 23 , 24 , 25 , 26 , 27 , 28 ]. The side chain of imidazole was also replaced by sulfur atom, etc.…”

Section: Resultsmentioning

confidence: 99%

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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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Section: Resultsmentioning

confidence: 99%

“…The solution was diluted with EtOAc (10 mL) and washed with H 2 O (3 × 10 mL). Then, the organic layer was separated and concentrated under vacuum, and the crude product was purified by column chromatography (petroleum ether/EtOAc) to provide the final product AI-27 [ 24 ].…”

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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“…Almost simultaneously, the Huang group reported a Fe III ‐catalyzed denitration approach to imidazo[1,2‐ a ]pyridines 339 through a one‐pot, three‐component reaction process involving 2‐aminopyridines ( 135 ), aldehydes 337 and nitroalkanes 338 , in moderate to good yields (Scheme ) 177. This report is an optimization of the procedure previously reported by the group that enabled the synthesis of 2‐aryl‐substituted 3‐methylimidazo[1,2‐ a ]pyridine derivatives in good yields from aminopyridines and substituted nitro olefins (see Scheme ) 150…”

Section: Cascade and Multicomponent Reactionsmentioning

confidence: 99%

Metal‐Catalyzed Cross‐Coupling Reactions of Aminopyridines

2015

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The aminopyridines are key building blocks in the synthesis of bioactive heterocyclic compounds such as azaindoles and imidazopyridines. The role of metal-catalyzed methods in aminopyridine functionalization, in particular the catalytic systems used, reaction conditions and the influence of aminopyridine substituents on the reaction outcome, is outlined. The review covers different metal-catalyzed reactions developed for C-C and C-N bond formation. One-pot and multicomponent reactions directed towards aminopyridine-

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“…14 Alternatively, different copper species have received considerable attention as catalysts for different kinds of organic transformations involving alkynes, such as homocoupling (Glaser-Hay coupling), [15][16][17][18] Huisgen 1,3-dipolar Cu I -catalyzed alkyne-azide cycloaddition, [19][20][21][22][23] Diels-Alder cycloadditions 24,25 and Sonogashira cross coupling. [26][27][28][29] Cu I salts were successfully applied as catalysts in the synthesis of imidazopyridines from aminopyridine and nitroolefines. 30 Other cyclization methods from aminopyridines involve the combination of Cu I and Pd II salts, as well as Cu I and In III under aerobic conditions.…”

Section: Introductionmentioning

confidence: 99%

Imidazo[1,2-a]pyridine A3-Coupling Catalyzed by a Cu/SiO2 Material

Salles¹,

Silva²,

Radatz³

et al. 2019

J. Braz. Chem. Soc.

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In this work, we report the preparation of a copper-silica material (Cu/SiO 2) by a sol-gel methodology and its characterization concerning composition and textural properties. The Cu/SiO 2 material was successfully applied as a Lewis acid heterogeneous catalyst for the A 3-coupling from 2-aminopyridine, aldehydes and alkynes to imidazo[1,2-a]pyridines (45-82%), which are relevant pharmacological scaffolds. The synthesis shows a number of advantages, such as easy separation from the reaction media and the minimal formation of metal aqueous wastes. Investigation of the mechanism supports the involvement of the formation of reaction intermediates inside the pores of the mesoporous material prior to 5-exo-dig cyclization.

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Iron(III)‐Catalyzed Denitration Reaction: One‐Pot Three‐Component Synthesis of Imidazo[1,2‐a]pyridine Derivatives

Cited by 64 publications

References 53 publications

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

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

Metal‐Catalyzed Cross‐Coupling Reactions of Aminopyridines

Imidazo[1,2-a]pyridine A3-Coupling Catalyzed by a Cu/SiO2 Material

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