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Study of the Effect of Substituents of ortho-Phenylenediamines in the Opening of Lactones and Lactams for Access to Benzimidazol-2-yl Alkanols and Benzimidazol-2-yl Alkylamines

Abstract : Benzimidazoles represent common chemical moieties in bioactive compounds. The synthesis of this heterocycle often involves a condensation of an ortho-phenylenediamine with a carboxylic acid derivative. The observed dialkylation of the starting ortho-phenylenediamine is avoided by opening of lactones or lactams. This strategy can directly yield 1H-benzimidazoles substituted at the 2-position by a functionalized chain. We present herein a study of the effect of different electron-withdrawing or electron-donating groups at the 4-position of ortho-phenylenediamines on the opening of lactones or lactams to synthesize benzimidazol-2-yl alkanols and benzimidazol-2-yl alkylamines.
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https://hal-pasteur.archives-ouvertes.fr/pasteur-03026011
Contributor : Martine Belin <>
Submitted on : Tuesday, December 15, 2020 - 9:18:41 AM
Last modification on : Wednesday, December 23, 2020 - 4:09:05 PM
Long-term archiving on: : Tuesday, March 16, 2021 - 6:41:23 PM

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Omar Castillo-Aguilera, Patrick Depreux, Alexia Ballée, Florian Beaurain, Paola Arimondo, et al.. Study of the Effect of Substituents of ortho-Phenylenediamines in the Opening of Lactones and Lactams for Access to Benzimidazol-2-yl Alkanols and Benzimidazol-2-yl Alkylamines. SYNLETT, Georg Thieme Verlag, 2020, 31 (12), pp.1216-1220. ⟨10.1055/s-0040-1707112⟩. ⟨pasteur-03026011⟩

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