Synlett 2020; 31(12): 1216-1220
DOI: 10.1055/s-0040-1707112
letter
© Georg Thieme Verlag Stuttgart · New York

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
a   Univ. Lille, CHU Lille, ULR 7365 - GRITA - Groupe de Recherche sur les formes Injectables et les Technologies Associées, 3 rue du Pr. Laguesse, 59000 Lille, France   Email: laurence.goossens@univ-lille.fr
b   Institut de Chimie Pharmaceutique Albert Lespagnol, 3 rue du Pr. Laguesse, 59000 Lille, France
,
Patrick Depreux
a   Univ. Lille, CHU Lille, ULR 7365 - GRITA - Groupe de Recherche sur les formes Injectables et les Technologies Associées, 3 rue du Pr. Laguesse, 59000 Lille, France   Email: laurence.goossens@univ-lille.fr
b   Institut de Chimie Pharmaceutique Albert Lespagnol, 3 rue du Pr. Laguesse, 59000 Lille, France
,
Alexia Ballée
a   Univ. Lille, CHU Lille, ULR 7365 - GRITA - Groupe de Recherche sur les formes Injectables et les Technologies Associées, 3 rue du Pr. Laguesse, 59000 Lille, France   Email: laurence.goossens@univ-lille.fr
b   Institut de Chimie Pharmaceutique Albert Lespagnol, 3 rue du Pr. Laguesse, 59000 Lille, France
,
Florian Beaurain
a   Univ. Lille, CHU Lille, ULR 7365 - GRITA - Groupe de Recherche sur les formes Injectables et les Technologies Associées, 3 rue du Pr. Laguesse, 59000 Lille, France   Email: laurence.goossens@univ-lille.fr
b   Institut de Chimie Pharmaceutique Albert Lespagnol, 3 rue du Pr. Laguesse, 59000 Lille, France
,
Paola B. Arimondo
c   Epigenetic Chemical Biology, Department of Structural Biology and Chemistry, Institut Pasteur, UMR3523 CNRS, 75015 Paris, France
,
Laurence Goossens
a   Univ. Lille, CHU Lille, ULR 7365 - GRITA - Groupe de Recherche sur les formes Injectables et les Technologies Associées, 3 rue du Pr. Laguesse, 59000 Lille, France   Email: laurence.goossens@univ-lille.fr
b   Institut de Chimie Pharmaceutique Albert Lespagnol, 3 rue du Pr. Laguesse, 59000 Lille, France
› Author Affiliations
This work was supported by the Centre National de la Recherche Scientifique (CNRS) and PlanCancer 2014 (N° EPIG201401) (to P.B.A), and by a PhD fellowship by the Ecole Doctorale Biologie Santé de Lille (EDBSL, France) National Council of Science and Technology (Consejo Nacional de Ciencia y Tecnología; CONACYT, Mexico) (to O.C.A.).
Further Information

Publication History

Received: 01 April 2020

Accepted after revision: 21 April 2020

Publication Date:
15 May 2020 (online)


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.

Supporting Information

 
  • References and Notes

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