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Probing N-Alkoxy Effects in Domino Reactions of α-Bromoacetamide Derivatives Towards Functionalized γ-Lactams

Abstract : The main objective of the present work is to better delineate the positive impact of N-alkoxy versus N-alkyl moieties in domino reactions. The key role of the metallic counterion of the basic reagent via a templating effect has been established, giving an insight over the superiority of N-alkoxy α-bromoacetamides compared to their N-alkyl analogues. The former demonstrated enhanced reactivity and efficiency, thus equiring milder conditions and leading to a wider scope of γ-lactams in good to excellent yields ranging from 67 to 98%. Overall, this study contributes to the emerging point of view that Nalkoxy nitrogenated compounds are useful building blocks with powerful but still under-developed synthetic potential, in particular in domino reactions.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-03808493
Contributor : Jean-François Brière Connect in order to contact the contributor
Submitted on : Monday, October 10, 2022 - 3:40:08 PM
Last modification on : Thursday, October 13, 2022 - 3:55:36 AM

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Philippe Champetter, Ismail Alahyen, Catherine Taillier, Jean-François Brière, Vincent Dalla, et al.. Probing N-Alkoxy Effects in Domino Reactions of α-Bromoacetamide Derivatives Towards Functionalized γ-Lactams. ChemistrySelect, 2022, 7 (38), ⟨10.1002/slct.202203305⟩. ⟨hal-03808493⟩

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