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. 2022 Nov 30;12(53):34496-34502.
doi: 10.1039/d2ra06070a. eCollection 2022 Nov 29.

Decarboxylative ring-opening of 2-oxazolidinones: a facile and modular synthesis of β-chalcogen amines

Fábio Z Galetto  1 , Cleiton da Silva  1 , Ricardo I M Beche  1 , Renata A Balaguez  1 , Marcelo S Franco  1 , Francisco F de Assis  1 , Tiago E A Frizon  2 , Xiao Su  3
Affiliations

Decarboxylative ring-opening of 2-oxazolidinones: a facile and modular synthesis of β-chalcogen amines

Fábio Z Galetto et al. RSC Adv. .

Abstract

We report herein the synthesis of primary and secondary β-chalcogen amines through the regioselective ring-opening reaction of non-activated 2-oxazolidinones promoted by in situ generated chalcogenolate anions. The developed one-step protocol enabled the preparation of β-selenoamines, β-telluroamines and β-thioamines with appreciable structural diversity and in yields of up to 95%.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Fig. 1
Fig. 1. (A) Structure of β-chalcogen amines; (B) structures of l-cysteine and l-selenocysteine; (C) examples of relevant synthetic β-Cas and their application fields.
Scheme 1
Scheme 1. Preparation of β-CAs and derivatives via 2-oxazolidinone decarboxylative ring-opening strategy: (A) synthesis of β-thioamines; (B) synthesis of β-CA derivatives from N-activated 2-oxazolidinones; (C) synthesis of β-CAs from non-activated 2-oxazolidinones (this work).
See this image and copyright information in PMC

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