HAL will be down for maintenance from Friday, June 10 at 4pm through Monday, June 13 at 9am. More information
Skip to Main content Skip to Navigation
Journal articles

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

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.
Document type :
Journal articles
Complete list of metadata

https://hal.univ-reims.fr/hal-03533721
Contributor : Pedro Lameiras Connect in order to contact the contributor
Submitted on : Tuesday, January 18, 2022 - 11:53:47 PM
Last modification on : Wednesday, May 18, 2022 - 9:33:11 AM

Identifiers

Collections

Citation

Amanda Garrido, Pierre-Olivier Delaye, François Quintin, Mohamed Abarbri, Pedro Lameiras, et al.. Direct Access to Highly Functionalised Benzimidazoles and Benzoxazoles from a Common Precursor. SYNTHESIS, Georg Thieme Verlag, 2019, 51 (21), pp.4006-4013. ⟨10.1055/s-0039-1690153⟩. ⟨hal-03533721⟩

Share

Metrics

Record views

31