T3P®-promoted Kabachnik-Fields reaction: An efficient synthesis of α-aminophosphonates

Tetrahedron Letters

Volumn 54, Issue 40, 2013, Pages 5430-5433

  Milen, Mátyás ^a,b   Ábrányi Balogh, Péter ^b   Dancsó, András ^a   Frigyes, Dávid ^a   Pongó, László ^a   Keglevich, György ^b  

^a EGIS PHARMACEUTICALS LTD   (Hungary)

^b BUDAPEST UNIVERSITY OF TECHNOLOGY AND ECONOMICS   (Hungary)

Author keywords

Aminophosphonates; Kabachnik Fields reaction; Mechanism; T3P ; Three component condensation

Indexed keywords

PHOSPHONIC ACID DERIVATIVE; T 3P; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; KABACHNIK FIELDS REACTION; POLYMERIZATION;

EID: 84883449729     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.07.145     Document Type: Article

References (68)

1. V.P. Kukhar, and H.R. Hudson Aminophosphonic and Aminophosphinic Acids: Chemistry and Biological Activity 2000 Wiley Chichester
2. P.P. Giannousis, and P.A. Bartlett J. Med. Chem. 30 1987 1603
3. M.C. Allen, W. Fuhrer, B. Tuck, R. Wade, and J.M. Wood J. Med. Chem. 32 1989 1652
4. P. Kafarski, and B. Lejczak Curr. Med. Chem. Anti-Cancer Agents 1 2001 301
5. F. Allerberger, and I. Klare J. Antimicrob. Chemother. 43 1999 211
6. A. Barder Aldrichim. Acta 21 1988 15
7. J. Emsley, and D. Hall Chemistry of Phosphorus 1976 Harper & Row London p 494
8. R. Hirschmann, A.B. Smith III, C.M. Taylor, P.A. Benkovic, S.D. Taylor, K.M. Yager, P.A. Sprengler, and S.J. Venkovic Science 264 1994 234
9. A.B. Smith III, C.M. Taylor, S.J. Benkovic, and R. Hirschmann Tetrahedron Lett. 35 1994 6853
10. V.P. Kukhar, and V.A. Solodenko Russ. Chem. Rev. (Engl. Transl.) 56 1987 859
11. S. Laschat, and H. Kunz Synthesis 1992 90
12. B. Kaboudin, and R. Nazari Tetrahedron Lett. 42 2001 8211
13. E.D. Matveeva, T.A. Podrugina, E.V. Tishkovskaya, L.G. Tomilova, and N.S. Zefirov Synlett 2003 2321
14. V.Y. Pavlov, M.M. Kabachinik, E.V. Zobnina, G.V. Ponomarev, and I.P. Beletskaya Synlett 2003 2193
15. E. Van Meenen, K. Moonen, D. Acke, and C.V. Stevens ARKIVOC i 2006 31 45 and references therein
16. M.I. Kabachnik, and T.Y. Medved Dokl. Akad. Nauk SSSr 83 1952 689 Chem. Abstr. 1953, 47, 2724b
17. E.K. Fields J. Am. Chem. Soc. 74 1952 1528
18. G. Keglevich, and E. Bálint Molecules 17 2012 12821
19. N.S. Zefirov, and E.D. Matveeva ARKIVOC i 2008 1
20. T. Akiyama, M. Sanada, and K. Fuchibe Synlett 2003 1463
21. C. Qian, and T. Huang J. Org. Chem. 63 1998 4125
22. R. Gallardo-Macias, and K. Nakayama Synthesis 2010 57
23. F. Xu, Y. Luo, M. Deng, and Q. Shen Eur. J. Org. Chem. 2003 4728
24. B.C. Ranu, A. Hajra, and U. Jana Org. Lett. 1 1999 1141
25. S. Chandrasekhar, S.J. Prakash, V. Jagadeshwar, and C. Narsihmulu Tetrahedron Lett. 42 2001 5561
26. A.S. Paraskar, and A. Sudalai ARKIVOC x 2006 183
27. K. Manabe, and S. Kobayashi Chem. Commun. 2000 669
28. J. Zon Polym. J. Chem. 55 1981 643
29. S. Lashat, and H. Kunz Synthesis 1992 90
30. J.S. Yadav, B.V.S. Reddy, and C. Madan Synlett 2001 1131
31. M.M. Kabachnik, E.V. Zobnina, and I.P. Beletskaya Synlett 2005 1393
32. M. Xia, and Y.D. Lu Ultrason. Sonochem. 14 2007 235
33. J.S. Yadav, B.V.S. Reddy, and P. Sreedhar Green Chem. 4 2002 436
34. S.T. Disale, S.R. Kale, S.S. Kahandal, T.G. Srinivasan, and R.V. Jayaram Tetrahedron Lett. 53 2012 2277
35. G. Keglevich, and A. Szekrényi Lett. Org. Chem. 5 2008 616
36. G. Keglevich, V.R. Tóth, and L. Drahos Heteroat. Chem. 22 2011 15
37. N.Z. Kiss, A. Kaszás, L. Drahos, Z. Mucsi, and G. Keglevich Tetrahedron Lett. 53 2012 207
38. E. Bálint, E. Fazekas, P. Pongrácz, L. Kollár, L. Drahos, T. Holczbauer, M. Czugler, and G. Keglevich J. Organomet. Chem. 717 2012 75
39. H. Wissmann, and H.-J. Kleiner Angew. Chem., Int. Ed. Engl. 19 1980 133
40. R. Escher, and P. Bünning Angew. Chem., Int. Ed. Engl. 25 1986 277
41. M. Schwarz Synlett 2000 1369
42. A.L.L. García Synlett 2007 1328
43. J.K. Augustine, A. Bombrun, A.B. Mandal, P. Alagarsamy, R.N. Atta, and P. Selvam Synthesis 2011 1477
44. J.K. Augustine, R. Kumar, A. Bombrun, and A.B. Mandal Tetrahedron Lett. 52 2011 1074
45. C. Madhu, Basavaprabhu, T.M. Vishwanatha, and V.V. Sureshbabu Tetrahedron Lett. 53 2012 1406
46. J.K. Augustine, A. Bombrun, W.H.B. Sauer, and P. Vijaykumar Tetrahedron Lett. 53 2012 5030
47. G. Nagendra, C. Madhu, T.M. Vishwanatha, and V.V. Sureshbabu Tetrahedron Lett. 53 2012 5059
48. K.M. Sharnababi, G. Nagendra, T.M. Vishwanatha, and V.V. Sureshbabu Tetrahedron Lett. 54 2013 478
49. M. Desroses, K. Wieckowski, M. Stevens, and L.R. Odell Tetrahedron Lett. 52 2011 4417
50. J.K. Augustine, A. Bombrun, and S. Venkatachaliah Tetrahedron Lett. 52 2011 6814
51. X. Wen, J.E. Bakali, R. Deprez-Poulain, and B. Deprez Tetrahedron Lett. 53 2012 2440
52. J.K. Augustine, A. Bombrun, B. Ramappa, and C. Boodappa Tetrahedron Lett. 53 2012 4422
53. S. Poojari, P.P. Naik, and G. Krishnamurthy Tetrahedron Lett. 53 2012 4639
54. K.S.S. Kumar, T.R. Swaroop, K.B. Harsha, K.H. Narasimhamurthy, and S. Rangappa Tetrahedron Lett. 53 2012 5619
55. J.K. Augustine, A. Bombrun, P. Alagarsamy, and A. Jothi Tetrahedron Lett. 53 2012 6280
56. M. Jida, and B. Deprez New J. Chem. 36 2012 869
57. A.B. Ramesha, G.M. Raghavendra, K.N. Nandeesh, K.S. Rangappa, and K. Mantelingu Tetrahedron Lett. 54 2013 95
58. M. Zarei Mendeleev Commun. 23 2013 29
59. S. Chandrasekhar, Ch. Narsihmulu, S.S. Sultana, B. Saritha, and S.J. Prakash Synlett 2003 505
60. K. Babak, and Z. Hazegh Chem. Lett. 37 2008 540
61. M.Z. Kassaee, F. Movahedi, and H. Masrouri Synlett 2009 1326
62. T. You-Ping, X. Feng, W. Yi, W. Jian-Jun, and L. Hui-Li J. Chem. Res. 2009 78
63. U. Gruss, and G. Hägele Phosphorus, Sulfur, Silicon 97 1994 209
64. A.A. Jafari, M. Nazarpour, and M. Abdollahi-Alibeik J. Heteroatom Chem. 21 2010 397
65. T. Thirumurugan, A. Nandakumar, N.S. Priya, D. Muralidaran, and P.T. Perumal Tetrahedron Lett. 51 2010 5708
66. R.R. Shagidullin, A.Kh. Plyamovatyi, R.M. Mukhamadeeva, V.K. Khairullin, and A.N. Pudovik Russ. J. Gen. Chem. 64 1994 833
67. N.S. Goulioukina, G.N. Bondarenko, S.E. Lyubimov, V.A. Davankov, K.N. Gavrilov, and I.P. Beletskaya Adv. Synth. Catal. 350 2008 482
68. Z. Mohamed, E. Abdelhakim, M. Abdessamad, R. Ahmed, and S. Said J. Chem. Res. 2005 324