Regioselective Synthesis of 2- and 3-Substituted Imidazo[1,2-<i>a</i>]pyridines

Liu, Shuai; Cong, Xuefeng; He, Jiaheng; Luo, Shi-Zhong; Wu, Di; Lan, Jingbo

doi:10.3184/174751912x13499663832261

Cited by 13 publications

(4 citation statements)

References 27 publications

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“…The solvent was removed in vacuo to afford 17 (0.487 g, 2.22 mmol, 98 %) (R f =0.32, 40 % EtOAc/hexane) as a yellow solid with no further purification required. Its characterisation corresponded to the literature [6a,30] …”

Section: Methodssupporting

confidence: 52%

Covalent Allosteric Inhibitors of Akt Generated Using a Click Fragment Approach

et al. 2022

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Akt is a protein kinase that has been implicated in the progression of cancerous tumours. A number of covalent allosteric Akt inhibitors are known, and based on these scaffolds, a small library of novel potential covalent allosteric imidazopyridine-based inhibitors was designed. The envisaged compounds were synthesised, with click chemistry enabling a modular approach to a number of the target compounds. The binding modes, potencies and antiproliferative activities of these synthesised compounds were explored, thereby furthering the structure activity relationship knowledge of this class of Akt inhibitors. Three novel covalent inhibitors were identified, exhibiting moderate activity against Akt1 and various cancer cell lines, potentially paving the way for future covalent allosteric inhibitors with improved properties.

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Section: Methodssupporting

confidence: 52%

Covalent Allosteric Inhibitors of Akt Generated Using a Click Fragment Approach

et al. 2022

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“…There have been scanty literature reports to-date for the synthesis of 3-aryl-imidazo[1,2- a ]pyridine derivatives. Relevant organic transformations for accessing these compounds are the condensation of 2-aminopyridine derivatives with α-halogen ketones, aldehydes, , alkynes, nitroolefins, or other functional species (Figure ) . In 2012, Lei showed the silver-mediated C–H/N-H oxidative cyclization for preparing arylimidazo[1,2- a ]pyridines .…”

Section: Introductionmentioning

confidence: 99%

Regioselective Direct C-3 Arylation of Imidazo[1,2-a]pyridines with Aryl Tosylates and Mesylates Promoted by Palladium–Phosphine Complexes

Choy

Luk

et al. 2015

J. Org. Chem.

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Direct C-3 arylation of imidazo[1,2-a]pyridines with aryl tosylates and mesylates has been accomplished by employing palladium(II) acetate associated with SPhos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl) or L1 (2-(2-(diisopropylphosphino)phenyl)-1-methyl-1H-indole). This catalyst system can be applied to a wide range of aryl sulfonates and shows excellent C-3 regioselectivity of imidazo[1,2-a]pyridine. These results represent the first examples of using tosylate- and mesylate-functionalized arenes as the electrophile partners for this regioselective direct arylation.

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“…Meanwhile, the tBCP+tBPB sample shows a more pronounced peak of Cl 2p. The pyridine rings in tBCP are prone to nucleophilic substitution reactions in the presence of leaving groups (halogens) in their ortho positions, 29,30 and tBPB acts as a nucleophile due to its electron-rich and lone pair of electron Lewis base properties (Fig. 1(a)), which makes it easier for tBCP to release chlorine radicals with the presence of tBPB.…”

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confidence: 99%