Synthesis and stereochemistry of new 1,3-thiazolidine systems based on 2-amino-2-(mercaptomethyl)propane-1,3-diol: 4,4-bis(hydroxymethyl)-1,3-thiazolidines and c-5-hydroxymethyl-3-oxa-7-thia-r-1-azabicyclo[3.3.0]octanes |
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Authors: | Cristina Morar Carmen Sacalis Pedro Lameiras Albert Soran Hassan Khartabil Cyril Antheaume Ioan Bratu Oana Moldovan Mircea Darabantu |
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Affiliation: | 1. “Babes-Bolyai” University, Department of Chemistry, 11 Arany János St., 400028 Cluj-Napoca, Romania;2. University of Reims Champagne-Ardenne, ICMR, UMR 7312, BP 1039, 51687 Reims, France;3. University of Strasbourg, Faculty of Pharmacy, 74 Rhin St., BP 60024, 67401 Illkirch Cedex, France;4. National Institute for Research and Development of Isotopic and Molecular Technologies (INCDTIM), 65-103, Donath St., PO Box 700, 400293 Cluj-Napoca 5, Romania |
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Abstract: | The thiaminalisation of 2-amino-2-(mercaptomethyl)propane-1,3-diol [‘2-(hydroxymethyl)cysteinol’] with aryl(di)aldehydes is reported. The resulting new class of 2-aryl-4,4-bis(hydroxymethyl)-1,3-thiazolidines is investigated by NMR and IR spectroscopy in tandem with DFT calculations, permitting structural assignments that are discussed in terms of conformational analysis, anomeric effects and ring-chain tautomerism. These acquired data are subsequently exploited. After treatment with formaldehyde, the subsequent (double) regio- and diastereoselective oxaminalisation of the 1,3-thiazolidine building-block affords the first non-symmetric series of a thiazolidin-oxazolidine fused system singly functionalised at the C-5 position. An unexpected rearrangement, which consists of the partial relocation of the Ar ligand from the 1,3-thiazolidine to the 1,3-oxazolidine ring, is observed as a major influence on the substitution of the Ar ring. The first single crystal X-ray analysis of the title bicyclic system, which discloses the homo- and/or heterochiral non-bonding interactions, is also presented. |
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Keywords: | Anomeric effect Cysteinols 1,3-Oxazolidines Ring-chain tautomerism 1,3-Thiazolidines |
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