Synthesis, Conformational Analysis and Crystal Structure of New Thioxo, Oxo, Seleno Diastereomeric Cyclophosphamides Containing 1,3,2-dioxaphosphorinane

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Author(s): Dorra Kanzari-Mnallah, Med Lotfi Efrit, Jiří Pavlíček, Frédéric Vellieux, Habib Boughzala, Azaiez Ben Akacha*.

Journal Name: Current Organic Chemistry

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Thioxo, Oxo, Seleno and diastereomeric cyclophosphamides containing 1,3,2-dioxaphosphorinane are prepared by a one-step chemical reaction. Their structural determination is carried out by means of Nuclear Magnetic Resonance NMR (31P, 1 H, 13C) and High-Resolution Mass Spectroscopy (HRMS). The conformational study of diastereomeric products is described. Density Functional Theory (DFT) calculations allowed the identification of preferred conformations. Experimental and calculated 31P, 13C, 1H NMR chemical shifts are compared. The molecular structure of the 2-Benzylamino-5-methyl-5-propyl-2-oxo-1,3,2-dioxaphosphorinane (3d) has been determined by means of crystal X-ray diffraction methods.

Keywords: Cyclophosphamide; diastereomeric 1, 3, 2-dioxaphosphorinane; NMR (31P, 1 H, 13C) analysis; DFT calculation; GIAO method; Xray structure.

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(E-pub Ahead of Print)
DOI: 10.2174/1385272823666190213142748
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