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CC BY-NC-ND 4.0 · SynOpen 2021; 05(04): 314-320
DOI: 10.1055/a-1681-4544
paper

Mild Biamidine-Transfer Conditions for the Synthesis of Aliphatic Biguanides

Rostyslav Bardovskyi‡
a   Université Côte d’Azur, ICN, UMR 7272 CNRS, 06108 Nice, France
,
Marie Fabre‡
a   Université Côte d’Azur, ICN, UMR 7272 CNRS, 06108 Nice, France
,
Cyril Ronco  ∗
a   Université Côte d’Azur, ICN, UMR 7272 CNRS, 06108 Nice, France
,
Rachid Benhida  ∗
a   Université Côte d’Azur, ICN, UMR 7272 CNRS, 06108 Nice, France
b   Mohamed VI Polytechnic University, UM6P, 43150 BenGuerir, Morocco
› Author AffiliationsThe authors are grateful for the financial support from the Research Fund of the Cancéropôle Provence-Alpes-Côte d'Azur (PACA) and the SATT-Sud Est (EmA grant – Emergence et Accompagnement). The Centre National de la Recherche Scientifique (CNRS), Université Côte d’Azur, ANR, and Région Sud are also acknowledged for additional funding.
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Abstract

This study focuses on the development of new synthetic pathways to monosubstituted biguanides from amines. An exhaustive comparison of the conditions and reagents used for biamidine transfer was performed. New reagents were synthesized and optimized conditions for the synthesis of substituted biguanides under mild conditions were developed. Eventually, two high-yielding and straightforward protocols for the transfer of a biamidine group to various amines are proposed and their scope and limitations have been explored. These conditions include: i) a direct chromatography-free procedure and ii) an eco-friendly procedure in water compatible with bioinspired molecules. They are particularly efficient for the demanding conversion of aliphatic amines.

Key words

biguanide - biamidine transfer - mild conditions - biocompatible protocol - guanidine derivatives

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1681-4544.
  • Supporting Information


Publication History

Received: 27 July 2021

Accepted: 06 August 2021

Accepted Manuscript online:
28 October 2021

Article published online:
18 November 2021

© 2021. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)

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