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 |
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| Authors: | Audrey MartinezJimmy Sé lambarom |
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| Affiliation: | a Université de La Réunion, Laboratoire de Chimie des Substances Naturelles et Sciences des Aliments (LCSNSA), FA 2212 15 avenue René Cassin BP 7151, F-97715 Saint-Denis Messageries Cedex 9, Reunion (France)
b Université de La Réunion, Groupe de Recherche Immunopathologies et maladies infectieuses (GRI), EA 4517 Plateau technique du CYROI, 2 Rue Maxime Rivière, BP 80 005, 97491 Sainte Clotilde Cedex 9, Reunion (France) |
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| 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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| Keywords: | Formaldehyde Prodrug Thiazolidine Oxazolidine One-pot |
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