Expedient Synthesis of 2-Iminothiazolidines via Telescoping Reactions Including Iron-Catalyzed Nitrene Transfer and Domino Ring-Opening Cyclization (DROC) - CNRS - Centre national de la recherche scientifique Accéder directement au contenu
Article Dans Une Revue European Journal of Organic Chemistry Année : 2021

Expedient Synthesis of 2-Iminothiazolidines via Telescoping Reactions Including Iron-Catalyzed Nitrene Transfer and Domino Ring-Opening Cyclization (DROC)

Résumé

2-iminothiazolidines are important scaffold for pharmaceutical drugs. Herein, we describe a fast and easy procedure for their synthesis by a telescoping reaction integrating an iron-catalyzed nitrene transfer under mild conditions. The aziridination reaction of olefins is followed by the domino ring-opening cyclization (DROC) of the aziridine intermediates with organic isothiocyanates catalyzed by a Lewis acid leading to the desired product. This new synthetic route allows time, step and purification economies, which is in agreement with the development of more efficient processes for the synthesis of small molecules.
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Dates et versions

hal-03102591 , version 1 (18-11-2021)

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Guillaume Coin, Oriane de Ferrier de Montal, Patrick Dubourdeaux, Jean-Marc Latour. Expedient Synthesis of 2-Iminothiazolidines via Telescoping Reactions Including Iron-Catalyzed Nitrene Transfer and Domino Ring-Opening Cyclization (DROC). European Journal of Organic Chemistry, 2021, 2021 (3), pp.443-448. ⟨10.1002/ejoc.202001379⟩. ⟨hal-03102591⟩
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