International Journal of Applied Science and Engineering
Published by Chaoyang University of Technology

Chia-Ling Lien and Chi-Tung Hsu1

Department of applied Chemistry, Chaoyang University of Technology, Wufong, Taichung County 41349, Taiwan, R.O.C.


 

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ABSTRACT


The synthesis of new derivatives 2 of α-hydrazino-(disubstituted)- alkylphosphonic acids by the Lewis acid mediated addition of dialkylphosphite to hydrazones, derived from benzoylhydrazine and aliphatic ketones, is described. Reactions were successfully and catalytically promoted by BF3 etherate under mild condition in methylene chloride at room temperature.


Keywords: Lewis acid; Nucleophilic addition; dialkylphosphite; α-hydrazinoalkylphosphonic acids; ketone hydrazones; benzoic acid hydrazides.


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REFERENCES


  1. [1] Baylis, E. K., Campbell, C. D., and Dingwall, J. G. 1984. α-Amino- phosphonous acids: a new class of biologically active amino acid analogs. ACS Symposium Series, 171 (Phosphorus Chem.): 183-186.

  2. [2] Takahashi H., Yoshioka M., Imai N., Onimura K., and Kobayashi S. 1994. Simple and improved preparation of -aminophosphonic acid derivatives, key building blocks of phosphono-peptides, Synthesis: 763-764.

  3. [3] Demir A. S., Tanyeli C., Sesenoglu O. l. Demic S., and Evin O. O. 1996. A simple synthesis of 1-aminophos- phonic acids from 1-hydroxyimino- phosphonates with NaBH4 in the presence of transition metal compounds. Tetrahedron Letters, 37: 407-410.

  4. [4] Sardarian A. R., and Kaboudin B. 1997. A    novel synthesis of diethyl 1-aminoarylmethylphosphonates on the surface of alumina. Tetrahedron Letters, 38: 2543-2546.

  5. [5] Atherton F. R., Hassall C. H., and Lambert R. W. 1986. Synthesis and structure-activity relationships of antibacterial phosphonopeptides incorporating (1-aminoethyl)-phosphonic acid and (aminomethyl)phosphonic acid. Journal of Medicinal Chemistry, 29: 29-40 and references cited therein.

  6. [6] Mao M. K., and Franz J. E. 1991. A facile general synthesis of thiocarboxylate S-esters of glyphosate and its derivatives. Synthesis: 920-922.

  7. [7] Maier L., and Sporri H. 1991. Organic phosphorus compounds.  96.  Resolution of 1-amino-2-(4-fluorophenyl) ethylphosphonic acid as well as some di- and tripeptides. Phosphorus, sulfur, and silicon and related Elements, 61: 69-75.

  8. [8] Huang J., and Chen R. 2000. An overview of recent advances on the synthesis and biological activity of -aminophosphonic acid derivatives. Heteroatom Chemistry, 11: 480-492.

  9. [9] Rachon, J., and Wasielewski, C. 1976. Aminophosphonic acids.  Part V. Syntheses of   α-aminophosphonic and α-hydrazinophosphonic acids from aliphatic aldazines. Roczniki Chemii., 50(3), 477-487.

  10. [10] Diel, P. J., and Maier, L. 1988. Organic phosphorus compounds. 84. Preparation, properties, and biological activity of (hydrazinomethyl) phosphonic and -phosphinic acids and derivatives. Phosphorus, Sulfur, and Silicon and the Related Elements: 36, 85-98.

  11. [11] Yuan, C., Chen, S., Xie, R., Feng, H., and Maier, L. 1995. Studies on organophosphorus compounds 94. Syntheses of 1-hydrazino- and 2-hydrazino-alkylph -osphonic acids and derivatives thereof. Phosphorus, Sulfur, and Silicon and the Related Elements, 106: 115-123.

  12. [12] Afarinkia, K., Rees, C. W., and Cadogan, J. I. G. 1990. Synthesis of organophosphorus compounds via silyl esters of phosphorus acids. Tetrahedron, 46: 7175-96.

  13. [13] Heydari, A., Javidan, A., and Schaffie, M. 2001. Lithium perchlorate/diethyl ether catalyzed one-pot synthesis of α-hydrazino- phosphonates from aldehydes by a three-component reaction. Tetrahedron Letters, 42: 8071-8073.

  14. [14] Schlemminger, I., Willecke, A., Maison, W., Koch, R., Lutzen, A., and Martens, J. 2001. Diastereo- selective Lewis acid mediated hydrophosphonylation of heterocyclic imines: a stereo- selective approach towards α-amino phosphonates, Journal of Chemical Society, Perkin Trans. I, 2804-2816.

  15. [15] Okimoto, M., and Chiba, T. 1990.  Electrochemical oxidation of ketone acylhydrazones and their hydrogen cyanide adducts in sodium cyanide- methanol. Transformation of ketones to nitriles. Journal of Organic Chemistry, 55: 1070-1076.

  16. [16] Cavill, J. L., Peters, J. U., and Tomkin-son, N. C. O. 2003. Iminium ion cataly-sis: Use of the α-effect in the accelera-tion of the Diels-Alder reaction. Chemi-cal Communications: 728-729.

  17. [17] Freifelder, M., Martin, W. B., Stone, G. R., Edwin L. C., and Coffin, L. 1961. The Preparation of 1-Halo- benzoyl-2-isopropylhydrazines. Selective Hy-drogenation of N=CH Function in the Presence of Aromatic Halogen, Journal of Orgainc Chemistry, 26: 383–386.


ARTICLE INFORMATION




Accepted: 2008-05-08
Available Online: 2008-04-01


Cite this article:

Lien, C.-L., Hsu, C.-T. 2008. Lewis Acid-catalyzed nucleophilic addition of dialkylphosphite to hydrazones derived from benzoylhydrazine and aliphatic ketones. International Journal of Applied Science and Engineering, 6, 11–17.https://doi.org/10.6703/IJASE.2008.6(1).11