Aminoimidazo[1,2-a]pyridines: regioselective synthesis of substituted imidazonaphthyridines, azacarbolines and cyclazines

Chezal, Jean‐Michel; Moreau, Emmanuel; Chavignon, Olivier; Gaumet, Vincent; Métin, J.; Blache, Yves; Diez, Anna; Fradera, Xavier; Luque, F. Javier; Teulade, Jean‐Claude

doi:10.1016/s0040-4020(01)01141-3

Cited by 23 publications

(7 citation statements)

References 34 publications

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“…Unfortunately, aminoimidazoles themselves or molecules featuring their fragments are rare. That is why there are only some examples where these compounds are used to complete the pyridine ring in the reaction with carbonyl compounds …”

Section: Figurementioning

confidence: 99%

“…That is why there are only some examples where these compounds are used to complete the pyridine ring in the reaction with carbonyl compounds. [11] In the literature some other examples are described, for example, an annelated imidazopyridine was prepared by selective reduction. [12] Saturated rings were annelated to imidazopyridines via a linker attached to the nitrogen atom of the imidazole ring.…”

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confidence: 99%

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Annelated Aminoimidazoles in Synthesis of Imidazo[4,5‐b]pyridines

et al. 2019

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A convenient method for the synthesis of annelated imidazo[4,5‐b]pyridines was developed. The method is based on condensation of previously unavailable aminoimidazoles with 1,3‐dicarbonyl compounds. Aminoimidazoles 3 were prepared and some their properties were studied. The method gives the target imidazopyridines in good yields and allow varying substituents. A set of imidazopyridines was prepared. As an example, the imidazopyridines featuring carboxylic acids and esters were synthesized. Their structure was unambiguously determined by multinuclear NMR spectroscopy and the molecular structure of imidazopyridine 15 a was determined by single‐crystal X‐Ray diffraction.

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Section: Figurementioning

confidence: 99%

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confidence: 99%

Annelated Aminoimidazoles in Synthesis of Imidazo[4,5‐b]pyridines

et al. 2019

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“…Synthesis of imidazopyridodiazepines 37-39 using a periannulation. [18] Scheme 10. Synthesis of benzodiazepin-2-ones 41 using Heck coupling reaction.…”

Section: Cà C Bond Formation Between Positions 5 Andmentioning

confidence: 99%

1,3‐Diazepine Derivatives: Strategies for Synthesis

2021

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“…Compounds like 44 are folic acid antagonists, and they exhibit diverse biological activity [37,38]. Various fused heterocyclic compounds 52-55 were synthesized by condensation of aminoimidazo[1,2-a]-pyridines 51a and 51b with aldehydes 1a and 1f [44] (Scheme 13). Alkyl-substituted imidazonaphthyridines 52 and 53, imidazodipyridines 54, and pyridoimidazodiazepines 55 can exhibit different kinds of pharmacological activity, in particular anticancer, genotoxic, anti-HIV, etc.…”

Section: Heterocyclesmentioning

confidence: 99%