The silver salt of 12-tungstophosphoric acid: an efficient catalyst for the three-component coupling of an aldehyde, an amine and an alkyne

Tetrahedron Letters

Volumn 47, Issue 43, 2006, Pages 7563-7566

  Mohan Reddy, K ^a   Seshu Babu, N ^a   Suryanarayana, I ^a   Sai Prasad, P S ^a   Lingaiah, N ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Acetonitrile; Propargylamine; Silver salt of 12 tungstophosphoric acid; Three component coupling

Indexed keywords

ALDEHYDE; ALKYNE; AMINE; PHOSPHOTUNGSTIC ACID; SILVER DERIVATIVE;

ARTICLE; CATALYST; DRUG SYNTHESIS; FILTRATION; INFRARED SPECTROSCOPY; ORGANIC CHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTITATIVE ANALYSIS; REACTION ANALYSIS; X RAY DIFFRACTION;

EID: 33748740815     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.08.094     Document Type: Article

References (48)

1. For representative monographs and reviews, see,. Wakefield B.J. Organomagnesium Methods in Organic Chemistry (1995), Academic Press
2. Blomberg C. The Barbier Reaction and Related One-Step Processes (1993), Springer
3. Lai Y.H. Synthesis (1981) 585-604
4. Courtois G., and Miginiac L. J. Organomet. Chem. 69 (1974) 1-44
5. Normant H. Adv. Org. Chem. 2 (1960) 1
6. Ioffe S.T., and Nesmeyanov A.N. The Organic Compounds of Magnesium, Beryllium, Calcium, Strontium and Barium (1976), North-Holland, Amsterdam
7. Loncaric C., Manabe K., and Kobayashi S. Adv. Synth. Catal. 345 (2003) 475-477
8. Patmore N.J., Hague C., Cotgreave J.H., Mahon M.F., Frost C.G., and Weller A.S. Chem. Eur. J. 8 (2002) 2088-2098
9. Longmire J.M., Wang B., and Zhang X. J. Am. Chem. Soc. 124 (2002) 13400-13401
10. Hayashi T., Uozumi Y., Yamazaki A., Sawamura M., Hamashima H., and Ito Y. Tetrahedron Lett. 32 (1991) 2799-2802
11. Yanagisawa A., Matsumoto Y., Asakawa K., and Yamamoto H. Tetrahedron 58 (2002) 8331-8339
12. Momiyama N., and Yamamoto H. J. Am. Chem. Soc. 125 (2003) 6038-6039
13. Zhang Y., Santos A.M., Herdtweck E., Mink J., and Kühn F.E. New J. Chem. 29 (2005) 366-370
14. Koseki Y., Omino K., Anzai S., and Nagasaka T. Tetrahedron Lett. 41 (2000) 2377-2380
15. Xu C., and Negishi E.I. Tetrahedron Lett. 40 (1999) 431-434
16. Wipf P., and Methot J.L. Org. Lett. 1 (1999) 1253-1255
17. Dalla V., and Pale P. New J. Chem. 23 (1999) 803-805
18. Yamasaki S., Fujii K., Wada R., Kanai M., and Shibasaki M. J. Am. Chem. Soc. 124 (2002) 6536-6537
19. Bates R.W., and Satcharoen V. Chem. Soc. Rev. 31 (2002) 12-21
20. Burgess K. Chem. Ind. 18 (1999) 716-717
21. Bianchini C., and Glendenning L. Chemtracts 10 (1997) 339-341
22. Itami K., Kamei T., Mineno M., and Yoshida J. Chem. Lett. (2002) 1084-1085
23. Ringdahl B. In: Brown J.H. (Ed). The Muscarinic Receptors (1989), Humana Press, Clifton, New Jersy
24. Zlotos D.P., Bender W., and Holzgrabe U. Exp. Opin. Ther. Patents 9 (1999) 1029
25. Kopka I.E., Fataftah Z.A., and Rathke M.W. J. Org. Chem. 45 (1980) 4616-4622
26. Imada Y., Yuassa M., Nakamura I.., and Murahashi S.I. J. Org. Chem. 59 (1994) 2282-2284
27. Czernecki S., and Valery J.M. J. Carbohydr. Chem. 9 (1990) 767-770
28. Fischer C., and Carreira E.M. Org. Lett. 3 (2001) 4319-4321
29. Li C.J., and Wei C. Chem. Commun. (2002) 268-269
30. Wei C., and Li C.J. J. Am. Chem. Soc. 124 (2002) 5638-5639
31. Koradin C., Polborn K., and Knochel P. Angew. Chem., Int. Ed. 41 (2002) 2535-2538
32. Shi L., Tu Y.Q., Wang M., Zhang F.M., and Fan C.A. Org. Lett. 6 (2004) 1001-1003
33. Wei C., and Li C.J. J. Am. Chem. Soc. 125 (2003) 9584-9585
34. Wei C., Li Z., and Li C.J. Org. Lett. 5 (2003) 4473-4475
35. Li Z., Wei C., Chen L., Varma R.S., and Li C.J. Tetrahedron Lett. 45 (2004) 2443-2446
36. Lo V.K.-Y., Liu Y., Wong M.-K., and Che C.-M. Org. Lett. 8 (2006) 1529-1532
37. Kozhevnikov I.V. Chem. Rev. 98 (1998) 171-198
38. Okuhara T., Mizuno N., and Misono M. Adv. Catal. 41 (1996) 113-252
39. Kozhevnikov I.V. Catalysis for Fine Chemicals, Catalysis by Polyoxometalates Vol. 2 (2002), Wiley, Chichester Chapter 7
40. Misono M. Chem. Commun. (2001) 1141-1152
41. Kozhevnikova E.F., Quartararo J., and Kozhevnikov I.V. Appl. Catal. A 245 (2003) 69-78
42. Firouzabadi H., and Jafari A.A. J. Iran. Chem. Soc. 2 (2005) 85 and references cited therein
43. Firouzabadi H., Iranpoor N., and Jafari A.A. Synlett (2005) 299
44. Moffat J.B. The Surface and Catalytic Properties of Heteropolyoxometalates (2001), Kluwer, New York
45. Rafiee E., Tork F., and Joshaghani M. Bioorg. Med. Chem. Lett. 16 (2006) 1221-1226
46. Yadav J.S., Reddy B.V.S., Praveenkumar S., Nagaiah K., Lingaiah N., and Saiprasad P.S. Synthesis 6 (2004) 901-904
47. Yadav J.S., Reddy B.V.S., Sridhar P., Reddy J.S.S., Nagaiah K., Lingaiah N., and Saiprasad P.S. Eur. J. Org. Chem. (2004) 552-557
48. Haber J., Pamin K., Matachowski L., Napruszewska B., and Poltowicz J. J. Catal. 207 (2002) 296-306