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

Authors

  • E. R. Abdurakhmanova Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine, Ukraine
  • О. V. Holovchenko Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine, Ukraine
  • V. S. Brovarets Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine, Ukraine

DOI:

https://doi.org/10.24959/ophcj.16.904

Keywords:

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

Abstract

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.

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References

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Published

2016-12-16

How to Cite

(1)
Abdurakhmanova, E. R.; Holovchenko О. V.; Brovarets, V. S. The Interaction of 1-Acetylamino-2,2-Dichlorethenylphosphonium Chlorides With Monoethanolamine. J. Org. Pharm. Chem. 2016, 14, 12-15.

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Section

Original Researches