Rapid synthesis of aliphatic amides by reaction of carboxylic acids, grignard reagent and amines: Application to the preparation of [11C]amides

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 19, 1997, Pages 2837-2842

  Aubert, Catherine ^a   Huard Perrio, Cécile ^a   Lasne, Marie Claire ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748592035     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a702897k     Document Type: Article

References (66)

1. A. L. Feliu, J. Chem. Educ., 1990, 67, 364.
2. D. Le Bars, S. K. Luthra, V. W. Pike and C. Luu Duc, Appl. Radiat. Isot., 1987, 38, 1073.
3. D. Le Bars, S. K. Luthra, V. W. Pike and E. R. Swenson, Appl. Radiat. Isot., 1988, 39. 671.
4. D. Le Bars; S. K. Luthra, V. W. Pike and K. L. Kirk, Appl. Radiat. Isot., 1988, 39, 287.
5. E. Ehrin, S. K. Luthra, C. Crouzel and V. W. Pike, J. Labelled Compd. Radiopharm., 1988, 25, 177.
6. S. K. Luthra, V. W. Pike and F. Brady, J. Chem. Soc., Chem. Commun., 1985, 1423.
7. D. W. McPherson, D. R. Hwang, J. S. Fowler, A. P. Wolf, R. M. MacGregor and C. D. Arnett, J. Labelled Compd. Radiopharm., 1986, 23, 505.
8. W. R. Banks, T. J. Tewson and G. A Digenis, J. Labelled Compd. Radiopharm., 1989, 26, 69.
9. W. R. Banks, T. J. Tewson and G. A. Digenis, Appl. Radiat. Isot., 1990, 41, 719.
10. S. K. Luthra, D. Le Bars, V. W. Pike and F. Brady, J. Labelled Compd. Radiopharm., 1989, 26, 66.
11. S. K. Luthra, V. W. Pike and F. Brady. Appl. Radiat., Isot., 1990, 41, 471.
12. J. A. McCarron, D. R. Turton and V. W. Pike, J. Labelled Compd. Radiopharm., 1996, 38. 941.
13. M.-C. Lasne, Ph. Cairon and L. Barré, Appl. Radiat. Isot., 1992, 43, 621.
14. Y. Andersson, M. Bergström and B. Langström, J. Labelled Compd. Radiopharm., 1994, 35, 98.
15. G. A. Rogers, S. Stone-Elander and M. Ingvar, J. Labelled Compd. Radiopharm., 1994, 35, 327.
16. K. Nagren and B. Langström, J. Labelled Compd. Radiopharm., 1989, 26. 83.
17. H. Yamazaki and N. Hayashi, Chem. Lett., 1993, 525.
18. M.-C. Lasne, B. Moreau, Ph. Cairon and L. Barré, J. Labelled Compd. Radiopharm., 1994, 34, 1165.
19. J. S. Fowler and A. P. Wolf, in Positron Emission Tomography and Autoradiography: principles and applications for the brain and heart, ed. M. Phelps, J. Mazziotta and H. Schelbert. Raven Press, New York, 1986.
20. T. Takashashi, T. Ido, R. Iwata, K. Hatano, H. Nakanishi, M. Shinohara and S. Iida, Appl. Radiat. Isot., 1988, 39, 659.
21. B. Langström, G. Antoni, P. Gullberg, C. Halldin, K. Nagren, A. Rimland and H. Svard, Appl. Radiat. Isot., 1986, 37, 1141.
22. G. Antoni and B. Langström, J. Labelled Compd. Radiopharm., 1987, 24, 125.
23. A. Rimland and B. Langström, Appl. Radiat. Isot., 1987, 38, 949.
24. Goethals, J. Sambre, G. Siegers and D. Van Haver, J. Labelled Compd. Radiopharm., 1989, 26, 256.
25. K. J. Fasth, P. Malmborg and B. Langström, J. Labelled Compd. Radiopharm., 1989, 26, 251.
26. K. J. Fasth, G. Antoni and B. Langström, Appl. Radiat. Isot., 1990, 41, 611.
27. B. C. Challis and J. A. Challis, in Comprehensive Organic Chemistry, ed. D. Barton and W. D. Ollis, Pergamon Press, Oxford, 1979, vol. 2, ch. 9.9, p. 957.
28. G. Benz, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon Press, Oxford, 1991, vol. 6, ch. 2.3, p. 381.
29. R. C. Larock, Comprehensive Organic Transformations, ed. VCH Publishers, New York, 1989, p. 972.
30. J. A. Mitchell and E. Reid, J. Am. Chem. Soc., 1931, 53, 1879.
31. B. S. Jursic and Z. Zdravkovski, Synth. Commun., 1993, 23, 2761.
32. P. Froyen, Synth. Commun., 1995, 25, 959.
33. M. Mader and P. Helquist, Tetrahedron Lett., 1988, 29, 3049.
34. R. Nomura, T. Nakano, Y. Yamada and H. Matsuda, J. Org. Chem., 1991, 56, 4076.
35. T. Ogawa, T. Hikasa, T. Ikegami, N. Ono and H. Suzuki, Chem. Lett., 1993, 815.
36. K. Ishihara, S. Ohara and H. Yamamoto, J. Org. Chem., 1996, 61, 4196.
37. H. Yazawa, K. Tanaka and K. Kariyone, Tetrahedron Lett., 1974, 3995.
38. C. Burnell-Curty and E. J. Roskamp, Tetrahedron Lett., 1993, 34, 5193.
39. E. Bon, D. C. H. Bigg and G. Bertrand, J. Org. Chem., 1994, 59, 4035.
40. K. Ishihara, Y. Kuroki, N. Hanaki, S. Ohara and H. Yamamoto, J. Am. Chem. Soc., 1996, 118, 1569.
41. J. Recht, B. I. Cohen, A. S. Goldman and J. Kohn, Tetrahedron Lett., 1990, 31, 7281.
42. K. Joshi, J. Bao, A. S. Goldman and J. Kohn, J. Am. Chem. Soc., 1992, 114, 6649.
43. A. Basha, M. Lipton and S. M. Weinreb, Tetrahedron Lett., 1977, 4171.
44. T. B. Sim and N. M. Yoon, Synlett, 1994, 827.
45. G. Chandra, T. A. George and M. F. Lappert, J. Chem. Soc. C, 1969, 2565.
46. L. A. Smith, W. B. Wang, C. Burnell-Curty and E. J. Roskamp, Synlett, 1993, 850.
47. K. W. Yang, J. G. Cannon and J. G. Rose, Tetrahedron Lett., 1970, 1791.
48. B. Singh, Tetrahedron Lett., 1971, 321.
49. R. Sanchez, G. Vest and L. Despres, Synth. Commun., 1989, 19, 2909.
50. M. F. Bodroux, Bull. Soc. Chim. Fr., 1905, 831.
51. H. L. Basset and C. R. Thomas, J. Chem. Soc., 1954, 1188.
52. C. Aubert, C. Huard and M.-C. Lasne, J. Labelled Compd. Radiopharm., 1995, 37, 87.
53. J. Fauvarque, J. Ducom and J. F. Fauvarque, C. R. Séances Acad. Soc. C, 1972, 511.
54. N. Ono, T. Yamada, T. Saito, K. Tanaka and A. Kaji, Bull. Chem. Soc. Jpn., 1978, 51, 2401.
55. J. K. Sutherland and D. A. Widdowson, J. Chem. Soc., 1964, 4650.
56. E. Bald, K. Saigo and T. Mukaiyama, Chem. Lett., 1975, 1163.
57. T. Mukaiyama, Y. Aikawa and S. Kobayashi, Chem. Lett., 1976, 57.
58. S. I. Shoda and T. Mukaiyama, Chem. Lett., 1980, 391.
59. J. Knol and B. L. Feringa, Synth. Commun., 1996, 26, 261.
60. A. Vogel, in Vogel's Textbook of Practical Organic Chemistry, ed. J. Wiley and Sons, New York, 1978, p. 366.
61. H. S. Lin and L. A. Paquette, Synth. Commun., 1994, 24, 2503.
62. A. P. Venkov and L. Lukanov, Synthesis, 1989, 59.
63. R. Gretler, E. Askitoglu, H. Kühne and M. Hesse, Helv. Chim. Acta, 1978, 61, 1730.
64. T. A. Crabb and S. L. Soilleux, J. Chem. Soc., Perkin Trans. 1, 1985, 1381.
65. Y. Watanabe, T. Ohta and Y. Tsuji, Bull. Chem. Soc. Jpn., 1983, 56, 2647.
66. H. Fritz, P. Hug, H. Sauter, T. Winkler and E. Logemann, Org. Magn. Reson., 1977, 9, 108.