3-Substituted 2-isocyanopyridines as versatile convertible isocyanides for peptidomimetic design

Charlie Hollanders; Mathias Elsocht; Olivier Van der Poorten; Mouhamad Jida; Evelien Renders; Bert U. W. Maes; Steven Ballet

doi:10.1039/D1CC01701B

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3-Substituted 2-isocyanopyridines as versatile convertible isocyanides for peptidomimetic design†

Charlie Hollanders,

‡^ab Mathias Elsocht,‡^a Olivier Van der Poorten,^a Mouhamad Jida,

^a Evelien Renders,^b Bert U. W. Maes

*^b and Steven Ballet

*^a

Author affiliations

* Corresponding authors

^a Research Group of Organic Chemistry, Departments of Chemistry and Bioengineering Sciences, Vrije Universiteit Brussel, Pleinlaan 2, Brussels 1050, Belgium
E-mail: steven.ballet@vub.be

^b Organic Synthesis Division, Department of Chemistry, University of Antwerp, Groenenborgerlaan 171, Antwerp 2020, Belgium

Abstract

We report the use of 3-substituted 2-isocyanopyridines as convertible isocyanides in Ugi four-component reactions. The N-(3-substituted pyridin-2-yl)amide Ugi products can be cleaved by amines, alcohols, and water with Zn(OAc)₂ as a catalyst. In addition, the applicability of the method was demonstrated in constrained di-/tripeptides bearing acid and base sensitive protective groups obtained via Ugi-4CR post-condensation modifications.

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Article information

DOI: https://doi.org/10.1039/D1CC01701B
Article type: Communication
Submitted: 30 Mar 2021
Accepted: 02 Jun 2021
First published: 15 Jun 2021

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Chem. Commun., 2021,57, 6863-6866

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3-Substituted 2-isocyanopyridines as versatile convertible isocyanides for peptidomimetic design

C. Hollanders, M. Elsocht, O. Van der Poorten, M. Jida, E. Renders, B. U. W. Maes and S. Ballet, Chem. Commun., 2021, 57, 6863 DOI: 10.1039/D1CC01701B

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Chemical Communications

3-Substituted 2-isocyanopyridines as versatile convertible isocyanides for peptidomimetic design†

Abstract

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3-Substituted 2-isocyanopyridines as versatile convertible isocyanides for peptidomimetic design

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