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 Access content directly
Journal Articles Tetrahedron Letters Year : 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

Abstract

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.

Dates and versions

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

Identifiers

Cite

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⟩
76 View
0 Download

Altmetric

Share

Gmail Mastodon Facebook X LinkedIn More