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Nguyen TB, Ermolenko L, Al-Mourabit A. Redox condensation of o-halonitrobenzene with 1,2,3,4-tetrahydroisoquinoline: involvement of an unexpected auto-catalyzed redox cascade. Chem Commun (Camb). 2016;52(27):4914-7doi: 10.1039/c6cc01436d.
Nguyen, T. B., Ermolenko, L., & Al-Mourabit, A. (2016). Redox condensation of o-halonitrobenzene with 1,2,3,4-tetrahydroisoquinoline: involvement of an unexpected auto-catalyzed redox cascade. Chemical communications (Cambridge, England), 52(27), 4914-7. https://doi.org/10.1039/c6cc01436d
Nguyen, T B, et al. "Redox condensation of o-halonitrobenzene with 1,2,3,4-tetrahydroisoquinoline: involvement of an unexpected auto-catalyzed redox cascade." Chemical communications (Cambridge, England) vol. 52,27 (2016): 4914-7. doi: https://doi.org/10.1039/c6cc01436d
Nguyen TB, Ermolenko L, Al-Mourabit A. Redox condensation of o-halonitrobenzene with 1,2,3,4-tetrahydroisoquinoline: involvement of an unexpected auto-catalyzed redox cascade. Chem Commun (Camb). 2016 Apr 07;52(27):4914-7. doi: 10.1039/c6cc01436d. Epub 2016 Mar 15. PMID: 26975797.
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Chem Commun (Camb). 2016 Apr 07;52(27):4914-7. doi: 10.1039/c6cc01436d. Epub 2016 Mar 15.

Redox condensation of o-halonitrobenzene with 1,2,3,4-tetrahydroisoquinoline: involvement of an unexpected auto-catalyzed redox cascade.

Chemical communications (Cambridge, England)

T B Nguyen, L Ermolenko, A Al-Mourabit

Affiliations

  1. Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Univ. Paris-Sud, Université Paris-Saclay, 1, av. de la Terrasse, 91198 Gif-sur-Yvette, France. [email protected].

PMID: 26975797 DOI: 10.1039/c6cc01436d

Abstract

A practical synthesis of fused benzimidazoles 5 has been developed by simply heating o-halonitrobenzenes 1 with tetrahydroisoquinolines 2. In this transformation, 2 played multiple roles as a building block, base and a double hydride donor in a cascade of uncatalyzed aromatic substitution, reduction of the nitro group, oxidation of the α-methylene group and condensation.

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