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

Omar Castillo-Aguilera (1, 2) , Patrick Depreux (1, 2) , Alexia Ballée (1, 2) , Florian Beaurain (1, 2) , Paola B Arimondo (3) , Laurence Goossens (1, 2)

1 GRITA - Groupe de Recherche sur les formes Injectables et les Technologies Associées - ULR 7365
2 ICPAL - Institut de Chimie Pharmaceutique Albert Lespagnol
3 EpiCBio - Chimie biologique épigénétique - Epigenetic Chemical Biology

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.

Keywords: 2-benzimidazol-2-yl alkanols; 2-benzimidazol-2-yl alkylamines; ortho-phenylenediamines; lactones; lactams

Domains: Chemical Sciences; Life Sciences [q-bio]

Omar Castillo-Aguilera, Patrick Depreux, Alexia Ballée, Florian Beaurain, Paola B 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, 2020, 31 (12), pp.1216-1220. ⟨10.1055/s-0040-1707112⟩. ⟨pasteur-03026011⟩