Synthese de 1,3,2-dioxaphosphorinanes diastereoisomeres: Influence de la conformation des 1,3-diols de depart sur leurs structures et conformations

<p></p> <p>1,3-Diol reacts with phosphorus trichloride to produce diastereomeric 1,3,2-dioxaphosphorinanes. To find the predominant conformations, the influence of the diol precursors is studied and density functional theory calculation (DFT) is used. Then, hydrolysis of chlorophosphite leads to two cyclodialcoxyphosphites which are identified by NMR (³¹P, <a href="#cit0001" target="_blank">¹</a> H, ¹³C, MR-SM). Also, the steps of synthesis of hydrazone 1-(5,5-diethyl-2-oxo-1,3,2-dioxaphosphoranyl)-3-phenyl-propanone are studied by ³¹P NMR.</p> <p><b>Résumé</b></p> <p>La conformation de départ du 1,3-diol influe sur la conformation des dérivés de 1,3,2-dioxaphosphorinane. En effet, l'addition du 1,3-diol sur le trichlorure de phosphore fournit un chloro-phosphite sous forme d'un mélange de diastéréoisomères. L'hydrolyse des deux chloro-phosphites conduit à deux cyclodialcoxyphosphites qui sont identifiés par RMN (³¹P, ¹H, ¹³C, GC-MS). Une étude de la synthèse de l'hydrazone β–phosphonatée est suivie par RMN du phosphore-31.</p

DFT, X-Ray cristallography and NMR analysis of new β-phosphonated thiosemicarbazones crystals

International audienceThiosemicarbazone compounds and their metal complexes exhibit noteworthyantiviral, antituberculous, antibacterial, and antitumor properties. Consequently, the synthesisof novel thiosemicarbazone ligands holds both theoretical and practical importance. In thiscontext, several phosphonated thiosemicarbazone ligands were synthesized by combiningβ-phosphonated hydrazones with organic isothiocyanates, as outlined in Scheme 1.All the synthesized products were structurally characterized using NMR spectroscopy, X-raycrystallography and DFT computing. An analysis of the crystal structures reveals theoccurrence of intra- and intermolecular hydrogen bonding