Synthesis 2019; 51(21): 4006-4013
DOI: 10.1055/s-0039-1690153
paper
© Georg Thieme Verlag Stuttgart · New York

Direct Access to Highly Functionalised Benzimidazoles and Benzoxazoles from a Common Precursor

Amanda Garrido
a   Laboratoire Synthèse et Isolement de Molécules Bioactives (SIMBA, EA 7502), Université de Tours, Faculté de Pharmacie, Parc de Grandmont, 31 Avenue Monge, 37200 Tours, France   Email: julien.petrignet@univ-tours.fr
,
Pierre-Olivier Delaye
a   Laboratoire Synthèse et Isolement de Molécules Bioactives (SIMBA, EA 7502), Université de Tours, Faculté de Pharmacie, Parc de Grandmont, 31 Avenue Monge, 37200 Tours, France   Email: julien.petrignet@univ-tours.fr
,
François Quintin
a   Laboratoire Synthèse et Isolement de Molécules Bioactives (SIMBA, EA 7502), Université de Tours, Faculté de Pharmacie, Parc de Grandmont, 31 Avenue Monge, 37200 Tours, France   Email: julien.petrignet@univ-tours.fr
,
Mohamed Abarbri
b   Laboratoire Physico-Chimie des Matériaux et des Electrolytes pour l’Energie (PCM2E, EA 6299), Université de Tours, Faculté des Sciences, Parc de Grandmont, 32 Avenue Monge, 37200 Tours, France
,
Pedro Lameiras
c   Institut de Chimie Moléculaire (ICMR CNRS UMR 7312), UFR Sciences Exactes et Naturelles BP 1039, 51687 Reims, France
,
Alain Gueiffier
a   Laboratoire Synthèse et Isolement de Molécules Bioactives (SIMBA, EA 7502), Université de Tours, Faculté de Pharmacie, Parc de Grandmont, 31 Avenue Monge, 37200 Tours, France   Email: julien.petrignet@univ-tours.fr
,
Jérôme Thibonnet
a   Laboratoire Synthèse et Isolement de Molécules Bioactives (SIMBA, EA 7502), Université de Tours, Faculté de Pharmacie, Parc de Grandmont, 31 Avenue Monge, 37200 Tours, France   Email: julien.petrignet@univ-tours.fr
,
Julien Petrignet
a   Laboratoire Synthèse et Isolement de Molécules Bioactives (SIMBA, EA 7502), Université de Tours, Faculté de Pharmacie, Parc de Grandmont, 31 Avenue Monge, 37200 Tours, France   Email: julien.petrignet@univ-tours.fr
› Author Affiliations
The authors are grateful to the French Ministry for Research and Innovation for the financial support.
Further Information

Publication History

Received: 01 July 2019

Accepted after revision: 22 July 2019

Publication Date:
06 August 2019 (online)


Abstract

Benzoxazole and benzimidazole are commonly encountered heterocycles in medicinal chemistry and their functionalisation around 1-, 2-, 5-, and/or 6-positions provides a wide range of molecules of biological interest. In this manuscript, a straightforward preparation of diversely and highly substituted benzimidazoles and benzoxazoles on these positions, from a common starting material, a 3,3-dibromoacrolein, is described. Such acrolein derivatives are almost never described in the literature or used as ‘building-block’ for organic synthesis. The double electrophilicity of this substrate was found to be advantageous for condensation with two equivalents of various 1,2-diaminobenzene or 2-aminophenol derivatives. This one-pot reaction performed under metal-free and mild conditions allows the creation of three new carbon–heteroatom bonds and affords the desired heterocycles.

Supporting Information

 
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