Regioselective Copper‐Catalyzed Oxidative Cross‐Coupling of Imidazo[1,2‐<i>a</i>]pyridines with Methyl Ketones: An Efficient Route for Synthesis of 1,2‐Diketones

Lei, Sai; Chen, Guijun; Mai, Yingying; Chen, Longbin; Cai, Haoyang; Tan, Jingwen; Cao, Hua

doi:10.1002/adsc.201500803

Cited by 79 publications

(14 citation statements)

References 93 publications

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“…One more example of synthesis of diketone from imidazopyridine and methyl ketone derivatives was reported by Lei and his co‐workers in 2016 (Scheme 59). [70] This ligand‐free Cu catalyzed synthesis was done in presence of acetic acid as an additive. Both electron‐rich and deficient imidazopyridine rings afford good yields of product.…”

Section: Functionalization Reactions Of Imidazo[1 2‐a]pyridinementioning

confidence: 99%

Recent Developments in Transition‐Metal‐Catalyzed Regioselective Functionalization of Imidazo[1, 2‐a]pyridine

Konwar

Bora

2021

ChemistrySelect

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Imidazo[1,2‐a]pyridine is an important nitrogen‐containing heterocycle from biological as well as pharmaceutical point of view. In recent years, regioselective functionalization of C−H bond of imidazo[1,2‐a]pyridine is extensively carried out using various transition metal‐based catalysts. Alkenylation, arylation, dual dehydrogenative annulations, formylation, thiolation, aminomethylation, dicarbonylation, phosphonylation along with other significant reactions are the progress in the field of functionalization of imidazopyridine. Most of these functionalizations are done at the C‐3 position of imidazo[1,2‐a]pyridine scaffold and in addition to that development towards C‐5 regioselectivity is also available. In this review, our aim is to present the recent advances for the functionalization of imidazo[1,2‐a]pyridine employing transition metal catalysts under significant reaction conditions.

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Section: Functionalization Reactions Of Imidazo[1 2‐a]pyridinementioning

confidence: 99%

Recent Developments in Transition‐Metal‐Catalyzed Regioselective Functionalization of Imidazo[1, 2‐a]pyridine

Konwar

Bora

2021

ChemistrySelect

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“…Cao and co-workers reported another interesting Cu (OAc) 2 -catalyzed dicarbonylation strategy on imidazo-[1,2-a]pyridines 1 using aryl methyl ketones 57 in toluene under oxygen atmosphere (Scheme 36). [56] Various substituted imidazo[1,2-a]pyridines reacted well with different ketones 57 and afforded corresponding 1,2-dicarbonylated products 58 in 10-93% yields. In this approach also, the additional oxygen atom came from molecular oxygen and not from water.…”

Section: Formylation and Carbonylationmentioning

confidence: 99%

Recent Advances in Radical C−H Bond Functionalization of Imidazoheterocycles

et al. 2020

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Direct CÀ H bond functionalization through radical pathway has emerged as a powerful and ideal strategy for the synthesis of organic compounds. This review provides an overview of recent developments in radical CÀ H functionalization of imidazoheterocycles such as imidazo[1,2-a] pyridine, benzo[d]imidazo[2,1-b]thiazole, imidazo [2,1-b]thiazole, imidazo[1,2-a]pyrimidine, imidazo [2,1-a]isoquinoline, imidazo[1,2-a]pyrazine and imidazo[1,2-a]quinoline using organic peroxides, photo/electric-induced protocols, iodine-based reagents, first-row transition metal catalysts (Fe, Mn, Ni and Cu) and inorganic oxidants/or

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“…Switching from DMSO to methyl ketones as coupling partner, 1,2-diketones 16 were isolated via the oxidative crosscoupling of imidazo[1,2-a]pyridines 14 in moderate to good yields (Scheme 7, Part B). 16 However, when R 2 was an electron-withdrawing group, no reaction occurred.…”

Section: Short Review Syn Thesismentioning

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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Regioselective Copper‐Catalyzed Oxidative Cross‐Coupling of Imidazo[1,2‐a]pyridines with Methyl Ketones: An Efficient Route for Synthesis of 1,2‐Diketones

Cited by 79 publications

References 93 publications

Recent Developments in Transition‐Metal‐Catalyzed Regioselective Functionalization of Imidazo[1, 2‐a]pyridine

Recent Developments in Transition‐Metal‐Catalyzed Regioselective Functionalization of Imidazo[1, 2‐a]pyridine

Recent Advances in Radical C−H Bond Functionalization of Imidazoheterocycles

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

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