KABACHNIK-FIELDS REACTIONS WITH 2,3-TRIMETHYLENE-1,2,3,4- TETRAHYDROHINAZOLON-4
In the article synthesized 2,3-trimethylene-3,4-dihydrohinazolon from anthranilic acid and pyrrolidone-2 in the presence different
agents, such as PCl 5 , POCl 3 . Its reduction reaction with NaBH 4 carrying out. Obtained 2,3-trimethylene-1,2,3,4-
tetrahydrohinazolon this three-component coupling of a carbonyl, an amine and a hydrophosphoryl compoud leads to α-
aminophosphonates, phosphorous acid-formaldehyde; aldehydes in three component system; aminomethylphosphonic acid
synthesis based on kabachnik-filds reaction. 2,3- trimethylene-3,4-dihydrohinazalon 55% da product obtained. The reason of low
reaction yield was studied. Structures were confirmed using IR and 1 H NMR spectroscopies. Obtained product reduced using
NaBH 4 and 2,3-trimethylene-1,2,3,4-tetrahydrohinazolon synthesis was carried out with high yield. 2,3- trimethylene-1,2,3,4-
tetrahydrohinazolon and respective aminophosphonic acids were synthesized in three component system with high yield.
1. E. Breuer, The Chemistry of Organophosphorus Compounds, vol. 4, John Wiley & Sons, New York, NY, USA, 1996.
2. Srinivasulu K., Anilkumar M., Nagaraju C., and Reddy C.S. “Synthesis and bioactivity of some new 2 substituted 3,4-dihidro-1-(9H-
carbazol-4-yloxy)methyl-3-[2-(2-methoxyphenoxy)ethyl]-1.3.2λ5-oxazaphosphole 2-oxides, sulfides and selenides,” Arkivoc, vol. 2007,
no. 14, pp. 100-109.
3. Prakasha T.K., Day R.O., and Holmes R.R., “New class of bicyclic oxyphosphoranes with an oxaphosphorinane ring: Molecular structures
and activation energies for ligand exchenge,” Journal of the American Chemical Society, vol. 116, no. 18, pp. 8095-8104, 1994.
4. Fest C.and Schmidt K.J., The Chemistry of Organophosphorus Pesticides, vol. 12, Springer, 1982.
5. Bhatia M.S. and Pawanjit P., “Phosphorus containing heterocycles as fungicides: synthesis of 2,2’ diphenylene chlorophosphonate and 2,2’
diphenylene chlorothiophosphonate”, Experientia, vol. 32, no. 9, p. 1111, 1976.
6. Manne P.N., Deshmukh S.D., Rao N.G.V., Dodale H.G., and Tikar S.N., “Efficacy of some insecticide against Helicoverpa armigera”,
Pestology, vol. 34, p 65, 2000.
7. Hendlin D., Stapley E. O., Jackson et al M. “Phosphonomycin, a new antibiotic produced by strains of Streptomyces”, Scence, vol. 166,
no. 3901, pp. 122-123, 1969.
8. Polozov A.M. and Cremer S.E., “Synthesis of 2H-1,2-oxaphosphorin 2-oxides”, Journal of Organometallic Chemistry, vol. 646, no. 1-2,
pp. 153-160, 2002.
9. Kukhar V.P. and Hundson H.R., Aminophosphonic and Aminophosphinic Acids: Chemistry and Biological Activity, John Wiley & Sons,
New York, NY, USA, 2000.
10. Huang J. and Chen R., “HYPERLINK an overview of recent advances on the synthesis and biological activity of αaminophosphonic acid
derivatives”, Heteroatom Chemistry, vol. 11, pp.480-492, 2000.
11. Quin L.D., A Guide to Organophosphorus Chemistry, vol. 11, Wiley, New York, NY, USA, 2000.
12. Hiratake J. and ODA J., “Aminophosphonic and aminoboronic acids as key elements of a trantsition state analogue inhibitor of enzymes,”
Bioscience, Biotechnology, and Biochemistry, vol. 61, no. 2, pp. 211-218, 1997.
13. Xiao L. X., Li K., and Shi D. Q., “A Convenient Synthesis and Herbicidal Activity of N-phosphonoalkylpyrazolo[4,3- e][1,2,4]-
triazolo[1,5-d]pyrimidines,” Phosphorus, Sulfur, and Silicon and the Related Elements, vol. 183, no. 12, pp. 3156-3165, 2008.
14. Allen M. C., Fuhrer W., Tuck B., Wade R., and Wood J. M., “Renin inhibitors. Synthesis of transition-state analogue inhibitiros containing
phosphorus acid derivatives at the scissile bond,” Journal of Medicinal Chemistry, vol. 32, no. 7, pp. 1652-1661, 1989.
15. Atherton F. R., Hassall C. H., and Lambert R. W., “Synthesis and structure-activity relationships of antibacterial phosphonpeptides
incorporating (1-aminoethyl) phosphonic acid and (aminomethyl) phosphonic acid,” journal of medicinal chemistry, vol. 29, no. l, pp. 29-
40, 1986.
16. Pratt R. F., “Inhibition of a class C β-lactamase by a specific phosphonate monoester,” Science, vol. 246, no. 4932, pp. 917-919, 1989.
17. Lavielle G., Hautefaye P., Schaffer C., Boutin J. A., Cudennec C. A., and Pierre A., “New α-amino phosphonic acid derivatives of
vinblastine: chemistry and antitumor activity,” Journal of medicinal chemistry, vol. 34, no. 7, pp. 1998-2003, 1991.
18. Kafarski P. and Lejczak B., “Biological activity of aminophosphonic acids,” phosphorus, Sulfur, and Silicon and the Related Elements,
vol. 63, no. 1-2, pp. 193-215, 1991.
19. Ria V.and Namboothiri I. N. N., “Enantioselective conjugate addition of dialkyl phosphites to nitroalkenes,” Tetrahedron Asymmetry, vol.
19, 20, pp. 2335-2338, 2008.
20. Kuliszewska E., Hanbauer M., and Hammerschmidt F., “preparation of α-aminobenzylphosphonic acids with a stereogenic quaternary
carbon atom via microscopically configurationally stable α-aminobenzyllithiums,” Chemistry A, vol. 14, no. 28, pp. 8603-8614. 2008.
21. Coeffard V., Beaudet I., Evain M., Grognec E. Le, and Quintard J. P., “Preparation and transmetallation of enantioenriched α-
aminoorganostannanes derived from N-boc phenylglycinol: Organic Chemistry, vol. 2008, no. 19, pp. 3344-3351, 2008.
22. Cherkasov R. A. and Galkin V. I., “The Kabachnik-fields reaction: synthetic potential and the problem of the mechanism,” Russian
Chemical Reviews, vol. 67, no. 10, pp. 587-882, 1998.
23. Zefirov N. S. and Matveeva E. D., “Catalytic Kabachnik-Fields reaction: new horizons for old reaction,” ARKIVOC, vol. 1, no. 11, pp. 1-
17, 2008.
24. Jacquier R., Hassani M. L., Petrus C., and Petrus F., “Asymmetric synthesis of 1-aminoalkylphosphonic acids,” Phosphorus, Sulfur, and
Silicon and the Releted Elements, vol. 81, no. 1-4, pp. 83-87, 1993.
25. Jommi G., Miglierini G., Pagliarin R., Sello G., and Sisti M., “Studies toward a model for predicting the diastereoselectivity in the
electrophilic amination of chiral 1,2,3-oxazaphospholanes,” Tetrahedron, vol. 48, no. 35, pp. 7275-7288, 1992.
26. Chakraborty, S. U. B. H. A. B. R. A. T. A., Mukerjee S., and Mukerjee S., "Effect of yttrium doping on the properties of bismuth ferrite: a
review." IJSST 3.1 (2013): 1-10.
27. Hannesian S.and Bennani Y., “Electrophilic amination and azidation of chiral α-alkyl phosphonamides: asymmetric syntheses of α-amino
α-alkyl phosphonic acids,” Synthesis, vol. 1994, no. 12, pp. 1272-1276, 1994.
28. Denmark S. E., Chatani N., and Pansare S. V., “Asymmetric electrophilic amination of chiral phosphorus-stabilized anions,” Tetrahedron,
vol. 48, no. 11, pp. 2191-2208, 1992.
29. El-Hashash, Maher A., And Sameh A. Rizk. "Behaviour Of 4-(4-Acetylaminophenyl)-4-Oxo-But-2-Enoic Acid Towards Carba-And Aza-
Nucleophiles And Some Reaction With The Products." Technology (Ijcpt) 3.2 (2013): 1-12.
30. Pudovik A. N., “New method of synthesis of esters of phosphonocarboxylic acids and their derivatives,” Doklady Akademii Nauk, vol. 85,
pp. 349-351, 1952.
31. Pudovik A. N. and Konovalova I.V., “Addition reactions of esters of phosphorus (III) acids with unsaturated systems,” Synthesis, vol.
1979, no. 2, pp. 81-96, 1979.
32. Kabachnik M. I. and Medvel T. Y., “New synthesis of aminophosphonic acids,” Doklady Akademii Nauk, vol. 83, pp. 689-692, 1952.
33. Fields E. K., “The synthesis of esters of substituted amino phosphonic acids,” Journal of the American Chemical Society, vol. 74, no. 6,
pp. 1528-1531, 1952.
34. Wiemer D. F., “Synthesis of nonracemic phosphonates,” Tetrahedron, vol. 53, no. 49, pp. 16609-16644, 1997.
35. Ranu B. C. and Hajra A., “A simple and green procedure for the synthesis of α-aminophosphonate by a one-pot threecomponent
condensation of carbonyl compound, amine and diethyl phosphite without solvent and catalyst,” Green Chemistry, vol. 4, no. 6, pp. 551-
554, 2002.
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