The interaction of 1-acetylamino-2,2-dichlorethenylphosphonium chlorides with monoethanolamine

E. R. Abdurakhmanova, О. V. Holovchenko, V. S. Brovarets


This paper presents the synthesis of new derivatives of 5-amino-2R-1,3-oxazol-4-iltriphenylphosphonium saltsand (acylamino-(3-methyl-1,3-oxazolidin-2-ylidene)methyl)triphenylphosphonium salts previously unknown. It has been shown that the interaction of available 1-acylamino-2,2-dichloroethenyltriphenylphosphonium chlorides with monoethanolamine leads only to formation of 4-phosphorylated 1,3-oxazole derivatives, which contain a residue of 2-hydroxyethylamine in position 5. Under similar conditions N-metylmonoethanolamine with 1-acylamino-2,2-dichloroethenyltriphenylphosphonium chlorides forms phosphorylated 2-methylen-1,3-oxazolidine derivatives, which contain the triphenylphosphonium group in the side chain. The structure of the new 2-R-5-(2-hydroxyethylamino)-1,3-oxazol-4-yltriphenyl- phosphonium perchlorates and (acylamino(3-methyl-1,3- oxazolidin-2-ylidene)methyl) triphenylphosphonium perchlorates has been reliably proven by elemental analysis, IR-, 1H NMR-, 13C-, 31P-spectroscopy and mass-spectrometry. In particular, derivatives of 1,3-oxazole have characteristic signals of carbon nuclei in 13C NMR-spectra, which appear as doublets due to the spin-spin interaction with a phosphorus nucleus. These signals are absent in 2-methylen-1,3-oxazolidine derivatives, but for these derivatives the signals of acylamino residues are characteristic. The synthetic method proposed is convenient and preparative since the transformation takes place in mild conditions to provide the final products with medium to high yields and does not require time-consuming purification operations of the final products.


1-acylamino-2,2-dihlorethenyltriphenylphosphonium chlorides; 1,3-oxazolidin-2-ylidenes; monoethanolamine; N-metylmonoethanolamine; 4-phosphorylated 5-amino-1,3-oxazoles; amino alcohols


Oxazoles / Ed. I. J. Turchi, New York: John Wiley, 1986, 1064 p. 2. Oxazoles: Synthesis, Reactions and Spectroscopy / Ed. D. C. Palmer, Hoboken: John Wiley, 2003, Pt A, 640 p. 3. Ross M. F., Kelso D. F., Bleyka F. Kh. Biokhimiya, 2005, Vol. 70, No.2, pp.273-284. 4. Drach B. S., Sviridov E. P., Kirsanov A. V. Zhurnal obshchey khimii, 1975, Vol. 45, No.1, pp.12-16. 5. Martynyuk A. P., Brovarets V. S., Lobanov O. P., Drach B. S. Zhurnal obshchey khimii, 1983, Vol. 54, No.10, pp.2186-2200. 6. Drach B. S., Sviridov E. P., Kisilenko A. A., Kirsanov A. V. Zhurnal obshchey khimii, 1973, Vol. 9, No.9, pp.1818-1824. 7. Brovarets V. S. (1999) Syntezy biorehuliatoriv heterotsyklichnoi pryrody na osnovi atsylaminozamishchenykh vinilfosfoniievykh solei ta yikh analohiv [Synthesis of heterocyclic nature bioregulators based acyl amino substituted vinyl phosphonium salts and their analogues] (PhD Thesis), Kyiv, Natsionalna akademiia nauk Ukrainy Instytut bioorhanichnoi khimii ta naftokhimii.

GOST Style Citations


Abbreviated key title: Ž. org. farm. hìm.

ISSN 2518-1548 (Online), ISSN 2308-8303 (Print)