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.

Autor: Castillo-Aguilera, Omar, Depreux, Patrick, Ballée, Alexia, Beaurain, Florian, Arimondo, Paola B., Goossens, Laurence
Předmět:
Zdroj: Synlett; 2020, Vol. 31 Issue 12, p1216-1220, 5p
Abstrakt: 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 1 H -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. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index