A novel one-pot, two-step synthesis of N-acyl-1,3-thiazolidines and N-acyl-1,3-oxazolidines as potential double prodrugs of formaldehyde - Université de La Réunion
Article Dans Une Revue Tetrahedron Letters Année : 2011

A novel one-pot, two-step synthesis of N-acyl-1,3-thiazolidines and N-acyl-1,3-oxazolidines as potential double prodrugs of formaldehyde

Résumé

A convenient and general one-pot, two-step protocol to prepare both N-acyl-1,3-thiazolidines and N-acyl-1,3-oxazolidines from formaldehyde, fatty acyl chlorides, and natural α-amino acids has been performed for the peculiar case of formaldehyde. In the presence of triethylamine to promote both the ring-forming process and the amide bond formation, subsequent addition of the acyl donor proved to be efficient to trap the preformed stable formaldehyde-derived 1,3-thiazolidine or the transient 1,3-oxazolidine using an appropriate ratio of formaldehyde.

Domaines

Chimie

Dates et versions

hal-01188124 , version 1 (28-08-2015)

Identifiants

Citer

Audrey Martinez, Jimmy Sélambarom. A novel one-pot, two-step synthesis of N-acyl-1,3-thiazolidines and N-acyl-1,3-oxazolidines as potential double prodrugs of formaldehyde. Tetrahedron Letters, 2011, 52 (13), pp.1444--1447. ⟨10.1016/j.tetlet.2011.01.049⟩. ⟨hal-01188124⟩
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