Synthesis and crystal structure of 7-(diethylamino)-2-ethoxy-3-(4-nitrophenyl)- 2H-benzo[e] [1,2]oxaphosphinin 2-oxide
DOI:
https://doi.org/10.15407/dopovidi2015.12.083Keywords:
organophosphorus, oxaphosphinin, phosphacoumarin, X-ray structureAbstract
A new member of 3-aryl phosphacoumarins has been synthesized by the Knoevenagel condensation of 4-(diethylamino)salicylaldehyde and diethyl 4-nitrobenzylphosphonate and the further cyclization. The title compound was fully characterized by NMR spectroscopy, high-resolution massspectrometry, and single crystal X-ray diffraction. Comparison of the molecular structures of synthesized phosphacoumarin and analogous coumarin is made by basing on the obtained data. Main structure features of the benzo[e] [1,2]oxaphosphinin fragment were analyzed in terms of the phosphorus influence.
Downloads
References
Sethna S. M., Shah N. M. Chem. Rev., 1945, 36: 1–62. https://doi.org/10.1021/cr60113a001
Peng X.-M., Damu G. L. V., Zhou C.-H. Curr. Pharm. Des., 2013, 19: 3884–3930. https://doi.org/10.2174/1381612811319210013
Zhang B., Ge C., Yao J., Liu Y., Xie H., Fang J. J. Am. Chem. Soc., 2015, 137: 757–769. https://doi.org/10.1021/ja5099676
Engel R. The use of carbon-phosphorus analogue compounds in the regulation of biological processes. Handbook of Orgnophosphorus Chemistry. New York: Marcel Dekker, 1992: 559–600.
The Chemistry of Organophosphorus Compounds, Ed. Hartley F.R., New York: Wiley, Vol. 4, 1996.
A Guide to Organophosphorus Chemistry. Ed. Quin L.D., Wiley: New York, 2000.
Chen C. H., Fox J. L., Lippert J. L. J. Heterocycl. Chem., 1987, 24: 931–932. https://doi.org/10.1002/jhet.5570240408
Bojilova A., Nikolova R., Ivanov C., Rodios N. A., Terzis A., Raptopoulou C. P. Tetrahedron, 1996, 52: 12597–12612. https://doi.org/10.1016/0040-4020(96)00748-X
Li X., Zhang D., Pang H., Shen F., Fu H., Jiang Y., Zhao Y. Org. Lett., 2005, 7: 4919-4922. https://doi.org/10.1021/ol051871m
Barton J. W., Buhaenko M„ Moyle B., Ratcliffe N. M. J. Chem. Soc., Chem. Commun., 1988, Iss. 7: 488–489. https://doi.org/10.1039/C39880000488
Knochel P., Normant J. F. J. Organomet. Chem., 1986, 309: 1–23. https://doi.org/10.1016/S0022-328X(00)99569-X
Yu T., Meng J., Zhang P., Zhao Y., Zhang H., Fan D., Chen L., Qiu Y. Spectrochim. Acta Mol. Biomol. Spectrosc., 2010, 75: 1036–1042. https://doi.org/10.1016/j.saa.2009.12.049
SADABS, Program for data collections, Bruker, AXS.
Sheldrick G. M. Acta Cryst., 2008, A64: 112–122. https://doi.org/10.1107/S0108767307043930
Downloads
Published
How to Cite
Issue
Section
License
Copyright (c) 2025 Reports of the National Academy of Sciences of Ukraine
This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.
