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.
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https://hal.univ-reunion.fr/hal-01188124
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Submitted on : Friday, August 28, 2015 - 3:06:59 PM
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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, Elsevier, 2011, 52 (13), pp.1444--1447. ⟨10.1016/j.tetlet.2011.01.049⟩. ⟨hal-01188124⟩

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