The kabachnik-fields reaction: Mechanism and synthetic use

Molecules

Volumn 17, Issue 11, 2012, Pages 12821-12835

  Keglevich, György ^a   Bálint, Erika ^a  

^a BUDAPEST UNIVERSITY OF TECHNOLOGY AND ECONOMICS   (Hungary)

Author keywords

aminophosphonates; Environmentally friendly; Kabachnik Fields reaction; Microwave; Reaction pathway; Solventes

Indexed keywords

DRUG CARRIER; PHOSPHINE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; SCHIFF BASE;

ANIMAL; CHEMICAL MODEL; CHEMISTRY; HUMAN; HYDROGEN BOND; MICROWAVE RADIATION; REVIEW; SYNTHESIS; THERMODYNAMICS;

ANIMALS; DRUG CARRIERS; HUMANS; HYDROGEN BONDING; MICROWAVES; MODELS, CHEMICAL; ORGANOPHOSPHONATES; PHOSPHINES; SCHIFF BASES; THERMODYNAMICS;

EID: 84870233145     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules171112821     Document Type: Review

References (51)

1. Kabachnik, M.I.; Medved, T.Y. New synthesis of aminophosphonic acids. Dokl. Akad. Nauk SSSR 1952, 83, 689-692.
2. Fields, E.K. The synthesis of esters of substituted amino phosphonic acids. J. Am. Chem. Soc. 1952, 74, 1528-1531.
3. Zefirov, N.S.; Matveeva, E.D. Catalytic Kabachnik-Fields reaction: New horizons for old reaction. ARKIVOC 2008, 1-17.
4. Kukhar, V.P., Hudson, H.R., Eds. Aminophosphonic and Aminophosphinic Acids: Chemistry and Biological Activity; Wiley: Chichester, UK, 2000.
5. Fields, S.C. Synthesis of natural products containing a C-P bond. Tetrahedron 1999, 55, 12237-12272.
6. Kafarski, P.; Lejczak, B. Aminophosphonic acids of potential medical importance. Curr. Med. Chem. Anticancer Agents 2001, 1, 301-312.
7. Bird, J.; De Mello, R.C.; Harper, G.P.; Hunter, DJ.; Karran, E.H.; Markwell, RE.; Miles-Williams, A.J.; Rahman, S.S.; Ward, R.W. Synthesis of novel N-phosphonoalkyl dipeptide inhibitors of human collagenase. J. Med. Chem. 1994, 37, 158-169.
8. Liu, W.S.; Rogers, C.J.; Fisher, A.J.; Toney, M.D. Aminophosphonate inhibitors of dialkylglycine decarboxylase: Structural basis for slow binding inhibition. Biochemistry 2002, 41, 12320-12328.
9. Mucha, A.; Kafarski, P.; Berlicki, L. Remarkable potential of the α-aminophosphonate/phosphinate structural motif in medicinal chemistry. J. Med. Chem. 2011, 54, 5955-5980.
10. Sienczyk, M.; Oleksyszyn, J. Irreversible inhibition of serine proteases-Design and in vivo activity of diaryl alpha-aminophosphonate derivatives. Curr. Med. Chem. 2009, 16, 1673-1687.
11. Grembecka, J.; Mucha, A.; Cierpicki, T.; Kafarski, P. The most potent organophosphorus inhibitors of leucine aminopeptidase. Structure-based design, chemistry, and activity. J. Med. Chem. 2003, 46, 2641-2655.
12. Long, N.; Cai, X.J.; Song, B.A.; Yang, S.; Chen, Z.; Bhadury, P.S.; Hu, D.Y.; Jin, L.H.; Xue, W. Synthesis and antiviral activities of cyanoacrylate derivatives containing an alpha-aminophosphonate moiety. J. Agric. Food Chem. 2008, 56, 5242-5246.
13. Hu, D.Y.; Wan, Q.Q.; Yang, S.; Song, B.A.; Bhadury, P.S.; Jin, L.H.; Yan, K; Liu, F.; Chen, Z.; Xue, W. Synthesis and antiviral activities of amide derivatives containing the alpha-aminophosphonate moiety. J. Agric. Food Chem. 2008, 56, 998-1001.
14. Danila, D.C.; Wang, X.Y.; Hubble, H.; Antipin, I.S.; Pinkhassik, E. Increasing permeability of phospholipid bilayer membranes to alanine with synthetic alpha-aminophosphonate carriers. Bioorg Med. Chem. Lett. 2008, 18, 2320-2323.
15. Cherkasov, R.A.; Galkin, V.I. The Kabachnik-Fields reaction: synthetic potential and the problem of the mechanism. Russ. Chem. Rev. 1998, 67, 857-882.
16. Galkin, V.I.; Zvereva, E.R.; Sobanov, A.A.; Galkina, I.V.; Cherkasov, R.A. Kinetics and mechanism of Kabachnik-Fields reaction in dialkylphosphite- benzaldehyde-aniline system. Zhur. Obsch. Khim. 1993, 63, 2224-2227.
17. Galkina, I.V.; Sobanov, A.A.; Galkin, V.I.; Cherkasov, R.A. Kinetics and mechanism of the Kabachnik-Fields reaction: IV. Salicyaldehyde in the Kabachnik-Fields reaction. Russ. J. Gen. Chem. 1998, 68, 1398-1401.
18. Matveeva, E.D.; Zefirov, N.S. On the mechanism of the Kabachnik-Fields reaction: Does a mechanism of nucleophilic amination of alpha- hydroxyphosphonates exist? Doklady Chem. 2008, 420, 137-140.
19. Galkina, I.V.; Galkin, V.I.; Cherkasov, R.A. Kinetics and the mechanism of Kabachnik-Fields reaction-V. Effect of the nature of hydrophosphoryl compound on the mechanism of Kabachnik-Fields reaction. Zhur. Obsch. Khim. 1998, 68, 1469-1475.
20. Gancarz, R.; Gancarz, I. Failure of aminophosphonate synthesis due to facile hydroxyphosphonate-phosphate rearrangement. Tetrahedron Lett. 1993, 34, 145-148.
21. Gancarz, R. Nucleophilic addition to carbonyl compounds. competition between hard (amine) and soft (phosphite) nucleophile. Tetrahedron 1995, 51, 10627-10632.
22. Keglevich, G; Fehérvári, A.; Csontos, I. A study on the Kabachnik-Fields reaction of benzaldehyde, propylamine and diethyl phosphite by in situ Fourier transform (FT) IR spectroscopy. Heteroatom Chem. 2011, 22, 599-604.
23. Keglevich, G.; Kiss, N.Z.; Menyhárd, D.; Fehérvári, A.; Csontos, I. A study on the Kabachnik-Fields reaction of benzaldehyde, cyclohexylamine and dialkyl phosphites. Heteroatom Chem. 2012, 23, 171-178.
24. Mu, X.-J.; Lei, M.-Y.; Zou, J.-P.; Zhang, W. Microwave-assisted solvent-free and catalyst-free Kabachnik-Fields reactions for α-amino phosphonates. Tetrahedron Lett. 2006, 47, 1125-1127.
25. Keglevich, G; Szekrényi, A. Eco-friendly accomplishment of the extended Kabachnik-Fields reaction; a solvent- and catalyst-free microwave-assisted synthesis of α-aminophosphonates and α-aminophosphine oxides. Lett. Org. Chem. 2008, 5, 616-622.
26. Matveeva, E.D.; Podrugina, T.A.; Tishkovskaya, E.V.; Tomilova, L.G; Zefirov, N.S. A novel catalytic three-component synthesis (Kabachnick-Fields reaction) of α-aminophosphonates from ketones. Synlett 2003, 2321-2324.
27. Bhagat, S.; Chakraborti, A.K. An extremely efficient three-component reaction of aldehydes/ketones, amines, and phosphites (Kabachnik-Fields reaction) for the synthesis of α-aminophosphonates catalyzed by magnesium perchlorate. J. Org. Chem. 2007, 72, 1263-1270.
28. 2 or molecular iodine. Org. Biomol. Chem. 2006, 4, 1663-1666.
29. Firouzabadi, H.; Iranpoor, N.; Sobhani, S. Metal triflate-catalyzed one-pot synthesis of α-aminophosphonates from carbonyl compounds in the absence of solvent. Synthesis 2004, 2692-2696.
30. Sun, P.; Hu, Z.; Huang, Z. Gallium triiodide catalyzed organic reaction: a convenient synthesis of α-amino phosphonates. Synth. Commun. 2004, 34, 4293-4299.
31. Ghosh, R.; Maiti, S.; Chakraborty, A.; Maiti, D.K. In(OTf)(3) catalysed simple one-pot synthesis of α-amino phosphonates. J. Mol. Catal. A 2004, 210, 53-57.
32. Bhattacharya, A.K.; Kaur, T. An efficient one-pot synthesis of alpha-amino phosphonates catalyzed by bismuth nitrate pentahydrate. Synlett 2007, 745-748.
33. Zhan, Z.-P.; Li, J.-P. Bismuth(III) chloride-catalyzed three-component coupling: Synthesis of alpha-amino phosphonates. Synth. Commun. 2005, 35, 2501-2508.
34. 3 in the synthesis of α-amino phosphonates via three-component reactions. Chin. J. Chem. 2006, 24, 1054-1057.
35. Xu, F.; Luo, Y.; Wu, J.; Shen, Q.; Chen, H. Facile one-pot synthesis of α-amino phosphonates using lanthanide chloride as catalyst. Heteroatom Chem. 2006, 17, 389-392.
36. Xu, F.; Luo, Y.; Deng, M.; Shen, Q. One-pot synthesis of α-amino phosphonates using samarium diiodide as a catalyst precursor. Eur. J. Org. Chem. 2003, 4728-4730.
37. Ravinder, K.; Vijender Reddy, A.; Krishnaiah, P.; Venkataramana, G; Niranjan Reddy, V.L.; Venkateswarlu, Y. CAN catalyzed one-pot synthesis of α-amino phosphonates from carbonyl compounds. Synth. Commun. 2004, 34, 1677-1683.
38. Ranu, B.C.; Hajra, A.; Jana, U. General procedure for the synthesis of α-amino phosphonates from aldehydes and ketones using indium(III) chloride as a catalyst. Org. Lett. 1999, 1, 1141-1143.
39. Lee, S.; Lee, J.K.; Song, CE.; Kim, D.-C. Microwave-assisted Kabachnik-Fields reaction in ionic liquid. Bull. Korean Chem. Soc. 2002, 23, 667-668.
40. Lee, S.; Park, J.H.; Kang, J.; Lee, J.K. Lanthanide triflate-catalyzed three component synthesis of α-amino phosphonates in ionic liquids. A catalyst reactivity and reusability study. Chem. Commun. 2001, 1698-1699.
41. Yadav, J.S.; Reddy, B.V.S.; Sreedhar, P. An eco-friendly approach for the synthesis of α-aminophosphonates using ionic liquids. Green Chem. 2002, 4, 436-438.
42. Prauda, I.; Greiner, I.; Ludányi, K.; Keglevich, G. Efficient synthesis of phosphono-and phosphinoxidomethylated N-heterocycles under solvent-free microwave conditions. Synth. Commun. 2007, 37, 317-322.
43. Keglevich, G; Szekrényi, A.; Sipos, M.; Ludányi, K.; Greiner, I. Synthesis of cyclic aminomethylphosphonates and aminomethyl- arylphosphinic acids by an efficient microwave-mediated phospha-Mannich approach. Heteroatom Chem. 2008, 19, 207-210.
44. Keglevich, G; Szekrényi, A.; Szöllösy, Á.; Drahos, L. Synthesis of bisp(hosphonatomethyl)-, bis(phosphinatomethyl)-, and bis(phosphinoxidomethyl)amines, as well as related ring bis(phosphine) platinum complexes. Synth. Commun. 2011, 41, 2265-2272.
45. 2)amine derivatives obtained by the double Kabachnik-Fields reaction with cyclohexylamine; Quantum chemical and X-ray study of the related bidentate chelate platinum complexes. Curr. Org. Chem. 2012, 16, 547-554.
46. Bálint, E.; Fazekas, E.; Pongrácz, P.; Kollár, L.; Drahos, L.; Holczbauer, T.; Czugler, M.; Keglevich, G. N-benzyl and N-aryl bis(phospha-Mannich adducts): Synthesis and catalytic activity of the related bidentate chelate platinum complexes in hydroformylation. J. Organomet. Chem. 2012, 717, 75-82.
47. Gourdel, Y.; Pelon, P.; Toupet, L.; Le Corre, M. Stereoselective synthesis of new functionalized bisphosphines. Tetrahedron Lett. 1994, 35, 1197-1200.
48. Keglevich, G.; Tóth, V. R.; Drahos, L. Microwave-assisted synthesis of α-hydroxy-benzylphosphonates and -benzylphosphine oxides. Heteroatom Chem. 2011, 22, 15-17.
49. Grün, A.; Molnár, I.G.; Bertók, B.; Greiner, I.; Keglevich, G. Synthesis of α-hydroxymethylenebisphosphonates by the microwave-assisted reaction of α-oxophosphonates and dialkyl phosphites under solventless conditions. Heteroatom Chem. 2009, 20, 350-354.
50. Keglevich, G; Grün, A.; Molnár, I.G.; Greiner, I. Phenyl-, benzyl- and unsymmetrical hydroxymethylenebisphosphonates as dronic acid ester analogues from α-oxophosphonates by microwave-assisted synthesis. Heteroatom Chem. 2011, 22, 640-648.
51. Kiss, N.Z.; Kaszás, A.; Drahos, L.; Mucsi, Z.; Keglevich, G A neighbouring group effect leading to enhanced nucleophilic substitution of amines at the hindered α-carbon atom of an α-hydroxyphosphonate. Tetrahedron Lett. 2012, 53, 207-209.