An efficient one-pot synthesis of pyrrolines and tetrahydropyridines from their chloro-precursors via in situ aza-Wittig reaction

Tetrahedron Letters

Volumn 46, Issue 24, 2005, Pages 4213-4217

  Singh, Pradeep N D ^a   Klima, Rodney F ^a   Muthukrishnan, Sivaramakrishnan ^a   Murthy, Rajesh S ^a   Sankaranarayanan, Jagadis ^a   Stahlecker, Heidi M ^a   Patel, Bhavika ^a   Gudmundsdóttir, Anna D ^a  

^a UNIVERSITY OF CINCINNATI   (United States)

Author keywords

Aza Wittig reaction

Indexed keywords

ALKANE DERIVATIVE; CHLORINE DERIVATIVE; PHOSPHITE; PYRIDINE DERIVATIVE; PYRROLINE DERIVATIVE; SODIUM AZIDE;

ARTICLE; MICROWAVE IRRADIATION; PRODUCTIVITY; SAFETY; SYNTHESIS; WITTIG REACTION;

EID: 19044393028     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.04.054     Document Type: Article

References (50)

1. B.E. Marayanoff, D.F. McComsey, J.F. Gardocki, R.P. Shank, M.J. Costanzo, S.O. Nortey, C.R. Schneider, and P.E. Setler J. Med. Chem 30 1987 1433
2. M.-G.A. Shvekhgeimer Chem. Heterocycl. Compd. 39 2003 405
3. N. De Kimpe, and M. Keppens J. Agric. Food Chem. 44 1996 1515
4. T.F. Favino, G. Gronza, C. Fuganti, D. Fuganti, P. Grasselli, and A. Mele J. Org. Chem. 61 1996 8975
5. P. Schieberle J. Agric. Food Chem. 43 1995 2442
6. P. Schieberle J. Agric. Food. Chem. 39 1991 141
7. R.G. Buttery, B.O. Juliano, and L. Ling Chem. Ind. 1983 478
8. R.L. Brahmachary, and M.P. Sarkar Nature 344 1990 26
9. C. Coindet, A. Comel, and G. Kirch Tetrahedron Lett. 42 2001 6101
10. J. Bielawski, S. Brandange, and L.J. Lindbolm J. Heterocycl. Chem. 15 1978 97
11. C.A. Zezza, M.B. Smith, B.A. Ross, A. Arhin, and P.L.E. Cronin J. Org. Chem. 49 1984 4397
12. D.H. Hua, S.W. Miao, S.N. Bharathi, T. Katsushira, and A.A. Bravo J. Org. Chem. 55 1990 3682
13. D.F. Fry, C.B. Fowler, and R.K. Dieter Synlett 1994 836
14. J. Boivin, E. Fouquet, and S.Z. Zard Tetrahedron Lett. 1990 85
15. A. Astier, and M.M. Plat Tetrahedron Lett. 1978 2051
16. B. Pugin, and L.M. Venanzi J. Am. Chem. Soc. 105 1983 6877
17. Y. Fukuda, S. Matsubura, and K. Utimoto J. Org. Chem. 56 1991 5812
18. P.H. Lambert, M. Vaultier, and R. Carrie J. Chem. Soc., Chem. Commun. 1982 1224
19. H. Staudinger, and I. Meyer Helv. Chim. Acta 2 1919 635
20. Y.G. Gololobov, I.N. Zhmurova, and L.F. Kasukhin Tetrahedron 37 1981 437
21. A. Alterman, and At. Hallberg J. Org. Chem. 65 2000 7984
22. For some recent reviews see U.R. Pillai, E. Sahle-Demessie, and R.S. Varma J. Mater. Chem. 12 2002 3199
23. L. Perreux, and A. Loupy Tetrahedron 57 2001 9199
24. R.S. Varma Pure Appl. Chem. 73 2001 193
25. P. Lidstrom, J. Tierney, B. Wathey, and J. Westman Tetrahedron 57 2001 9225
26. A. Diaz-Ortiz, A. de la Hoz, and F. Langa Green Chem. 2 2000 165
27. K. Tanaka, and F. Toda Chem. Rev. 100 2000 1025
28. S. Deshayes, M. Liagre, A. Loupy, J.-L. Luche, and A. Petit Tetrahedron 55 1999 10851
29. R.S. Varma Green Chem. 1 1999 43
30. A. Loupy, A. Petit, J. Hamelin, F. Texier-Boullet, P. Jacquault, and D. Mather Synthesis 1998 1213
31. S. Caddick Tetrahedron 51 1995 10403
32. P.N.D. Singh, C.L. Carter, and A.D. Gudmundsdóttir Tetrahedron Lett. 44 2003 6763
33. P.N.D. Singh, S. Muthukrishnan, R.S. Murthy, R.F. Klima, S.M. Mandel, M. Hawk, N. Yarbrough, and A.D. Gudmundsdóttir Tetrahedron Lett. 44 2003 9169
34. -1
35. We used a conventional microwave oven, 2450 MHz, 1100 W
36. M.C. Law, L.-Y. Wong, and T.H. Chan Green Chem. 4 2002 328
37. A.E. Kemppainen, M.J. Thomas, and P.J. Wagner J. Org. Chem. 41 1976 1294
38. S.-S. Cheng, C. Piantadosi, and J.L. Irvin J. Pharm. Sci. 57 1968 1910
39. W. Koller, and P. Schlack Chem. Ber. 96 1963 93
40. J.H. Burckhalter, and J.H. Short J. Org. Chem. 23 1958 1278
41. +)
42. N. De Kimpe, K.A. Tehrani, C. Stevens, and P. De Cooman Tetrahedron 53 1997 3693
43. N. De Kimpe, E. Stanoeve, and M. Boyeykens Synthesis 1994 4427
44. N. De Kimpe, and C. Stevens Tetrahedron 51 1995 2387
45. 3): 1.16 (d, 6 Hz, 6H), 1.88 (s, 3H), 1.41 (s, 3H), 3.26 (s, 6H), 3.75 (septet, 6 Hz, 1H) ppm
46. 3): 1.16 (d, 6 Hz, 6H), 1.40 (s, 3H), 3.20 (s, 6H), 1.5-1.7 (m, 2H), 1.8-2.0 (m, 2H), 2.2-2.5 (m, 2H), 3.57 (t, 6.5 Hz, 2H), 3.70 (septet, 6 Hz, 1H) ppm
47. 3): 1.26 (s, 3H), 1.5-1.9 (m, 4H), 2.57 (t, 6 Hz, 2H), 3.18 (s, 6H), 3.52 (t, 6.5 Hz, 2H) ppm
48. 3): 1.36 (s, 3H), 1.5-1.8 (m, 4H), 2.65 (t, 2H), 3.24 (s, 6H), 3.3 (m, 2H) ppm
49. 3): 1.42 (s, 3H), 1.4-1.8 (m, 4H), 2.0-2.2 (m, 2H), 3.25 (s, 6H), 3.6-3.9 (m, 2H) ppm
50. 3): 1.4-2.0 (m, 4H), 2.3 (m, 2H), 2.37 (s, 3H) 3.5-4.0 (m, 2H) ppm