Synthesis, Conformational Analysis and Crystal Structure of New Thioxo, Oxo, Seleno Diastereomeric Cyclophosphamides Containing 1,3,2-dioxaphosphorinane-Reference-Cited by-同舟云学术

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

Published:2019-04-23 Issue:2 Volume:23 Page:205-213
ISSN:1385-2728
Container-title:Current Organic Chemistry
language:en
Short-container-title:COC

Author:

Kanzari-Mnallah Dorra¹,Efrit Med L.¹,Pavlíček Jiří²,Vellieux Frédéric²,Boughzala Habib³,Akacha Azaiez B.¹

Affiliation:

1. Laboratory of Selective Organic and Heterocyclic Synthesis-Biological Activity Evaluation, Department of Chemistry, Faculty of Science of Tunis, University Tunis El Manar, 2092 Tunis, Tunisia

2. Centre of Molecular Structure Institute of Biotechnology CAS, v.v.i. Biocev. Prumyslova, 595 252 50 Vestec, Czech Republic

3. Preparatory Institute for engineering studies, 8000 Nabeul, Tunisia

Abstract

Thioxo, Oxo and Seleno 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 Xray diffraction methods.

Publisher

Bentham Science Publishers Ltd.

Subject

Organic Chemistry

Reference40 articles.

1. Bentrude WG, Hargis JHD. J Chem Soc, Conformations of 6-membered-ring phosphorus hetrerocycles: the 5-t-butyl-2-oxo-1,3,2-dioxaphosphorinanes.,, 1969, 19,, 1113-1114,

2. Bentrude WG, Tan HW. J Chem Soc, Conformations of saturated cyclic phosphorus heterocycles II. 5-tert-butyl-2-amino-1,3,2-dioxaphosphorinanes apparent effects of P-N vicinal interactions on the conformational energy of amino groups on trivalent phosphorus and the influence of lone pair orientation.,, 1973, 95,, 4666-4675,

3. Day RO, Bentrude WG, Yee KC, Setzer WN, Deiters JA, Holmes RR. J Am Chem Soc, The first monocyclic 1,3,2-dioxaphosphorinane in a boat form: synthesis, structure and stability.,, 1984, 106,, 103-106,

4. Bajwa GS, Chandrasekaran S, Hargis JH, Sopchik AE, Blatter D, Bentrude WG. J Am Chem Soc, Conformations of saturated six-membered ring phosphorus heterocycles. Cis- and trans-2-oxo- and 2-thio-2- (dimethylamino)-5-tert-butyl-1,3,2-oxazaphosphorinanes: Molecules related to cyclophosphamide.,, 1982, 104,, 6385-6392,

5. Setzer WN, Sopchik AE, Bentrude WG. J Am Chem Soc, Conformations of saturated six-membered-ring phosphorus heterocycles. Chair-chair equilibria for cyclophosphamide, the 5,5-dimethyl derivative, and related 1,3,2-oxazaphosphorinanes.,, 1985, 107,, 2083-2091,

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