Sodium borohydride on wet clay: Solvent-free reductive amination of carbonyl compounds using microwaves

Tetrahedron

Volumn 54, Issue 23, 1998, Pages 6293-6298

  Varma, Rajender S ^a   Dahiya, Rajender ^a  

^a SAM HOUSTON STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL DERIVATIVE; ENAMINE; IMINE; SODIUM BOROHYDRIDE; TERTIARY AMINE;

AMINATION; ARTICLE; CLAY; DRUG STRUCTURE; DRUG SYNTHESIS; MICROWAVE IRRADIATION; PRIORITY JOURNAL; REACTION TIME; REDUCTION; STRUCTURE ANALYSIS;

EID: 0032482298     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00326-3     Document Type: Article

References (69)

1. 1. (a) Emerson, W. S. Organic Reactions, Wiley, New York, 1948, vol. 4, chapter 3, pp 174.
2. (b) Hutchins, R. O.; Natale, N. Org. Prep. Proced. Int. 1979, 11, 20.
3. (c) Lane, C. F. Synthesis 1975, 135.
4. (d) Hudlicky, M. Reductions in Organic Chemistry, Second Ed., ACS Monograph 188, 1996, pp 187 and references cited therein.
5. (e) Reductions in Organic Synthesis, Abdel-Magid, A. F., Ed., ACS Symposium Series 641; American Chemical Society, Washington DC, 1996, pp 201.
6. (f) Ranu, B. C.; Sarkar, A.; Majee, A. J. Org. Chem. 1997, 62, 1841.
7. 2. Luthardt, H.; Fieseler, C.; Wind, M.; Biering, H.; Kochmann, W.; Kramer, W.; Manmen, H.; Roethling, T. Ger. Patent 237,250, 1976; Chem. Abstr. 1976, 107, 35133a.
8. 2. Luthardt, H.; Fieseler, C.; Wind, M.; Biering, H.; Kochmann, W.; Kramer, W.; Manmen, H.; Roethling, T. Ger. Patent 237,250, 1976; Chem. Abstr. 1976, 107, 35133a.
9. 3. Worbel, J. E.; Ganem, B. Tetrahedron Lett. 1981, 22, 3447 and references cited therein.
10. 4. Borch, R. F.; Bernstein, M. D.; Durst, H. D. J. Am. Chem. Soc. 1971, 93, 2897.
11. 5. Abdel-Magid, A. F.; Carson, K. G.; Harris, B. D.; Maryanoff, C. A.; Shah, R. D. J. Org. Chem. 1996, 61, 3849 and references cited therein.
12. 6. Giancarlo, V.; Giumanini, A. G.; Strazzolini, P.; Poiana, M. Synthesis 1993, 121.
13. 7. (a) Balogh, M.; Laszlo, P. Organic Chemistry Using Clays; Springer-Verlag: Berlin, 1993.
14. (b) Laszlo, P. Preparative Chemistry using Supported Reagents, Academic Press, San Diego, California, 1987.
15. (c) McKillop, A.; Young, D. W. Synthesis 1979, 401 and 481.
16. (d) Posner, G. H. Angew. Chem. 1978, 90, 527; Angew. Chem. Int. Ed. Engl. 1978, 17, 487.
17. (d) Posner, G. H. Angew. Chem. 1978, 90, 527; Angew. Chem. Int. Ed. Engl. 1978, 17, 487.
18. (e) Kabalka, G. W.; Wadgaonkar, P. P.; Chatla, N. Synth. Commun. 1990, 20, 293.
19. (f) Kabalka, G. W.; Pagni, R. M. Tetrahedron 1997, 53, 7999.
20. 8. For recent reviews on microwave assisted chemical reactions see (a) Abramovich, R. A. Org. Prep. Proced. Int. 1991, 23, 683.
21. (b) Whittaker, A. G.; Mingos, D. M. P. J. Microwave Power Electromagn. Energy 1994, 29, 195.
22. (c) Majetich, G.; Hicks, R. J. Microwave Power Electromagn. Energy 1995, 30, 27.
23. (d) Caddick, S. Tetrahedron 1995, 51, 10403.
24. (e) Varma, R. S. "Microwave-Assisted Reactions under Solvent-Free 'Dry' Conditions" in Microwaves: Theory and Application in Material Processing IV, Clark, D. E.; Sutton, W. H.; Lewis, D. A., Eds., American Ceramic Society, Ceramic Transactions 1997, 80, pp 375-365.
25. 9. (a) Gedye, R.; Smith, F.; Westaway, K.; Ali, H.; Baldisera, L.; Laberge, L.; Rousell, J. Tetrahedron Lett. 1986, 27, 279.
26. (b) Giguere, R. J.; Namen, A. M.; Lopez, B. O.; Arepally, A.; Ramos, D. E.; Majetich, G.; Defrauw, J. Tetrahedron Lett. 1987, 28, 6553.
27. (c) Bose, A. K.; Banik, B. K.; Lavlinskaia, N.; Jayaraman, M.; Manhas, M. S. Chemtech 1997, 27, 18.
28. 10. (a) Oussaid, A.; Thach, L. N.; Loupy, A. Tetrahedron Lett. 1997, 38, 2451.
29. (b) Villemin, D.; Alloum, A. B. Synth. Commun. 1991, 21, 63.
30. (c) Lerestif, J. M.; Toupet, L.; Sinbandhit, S.; Tonnard, F.; Bazureau, J. P.; Hamelin, J. Tetrahedron 1997, 53, 6351.
31. 11. For cleavage-deprotection reactions see: (a) Varma, R. S.; Chatterjee, A. K.; Varma, M. Tetrahedron Lett. 1993, 34, 3207.
32. (b) Varma, R. S.; Chatterjee, A. K.; Varma, M. Tetrahedron Lett. 1993, 34, 4603.
33. (c) Varma, R. S.; Varma, M.; Chatterjee, A. K. J. Chem. Soc., Perkin. Trans. 1 1993, 999.
34. (d) Varma, R. S.; Lamture, J. B.; Varma, M. Tetrahedron Lett. 1993, 34, 3029.
35. (e) Varma, R. S.; Saini, R. K. Tetrahedron Lett. 1997, 38, 2623.
36. (f) Varma, R. S.; Meshram, H. M. Tetrahedron Lett. 1997, 38, 5427.
37. (g) Varma, R. S.; Meshram, H. M. Tetrahedron Lett. 1997, 38, 7973.
38. (h) Varma, R. S.; Dahiya, R.; Saini, R. K. Tetrahedron Lett. 1997, 38, 8819. For condensation-cyclization reactions see:
39. (i) Varrna, R. S.; Dahiya, R.; Kumar, S. Tetrahedron Lett. 1997, 38, 2039.
40. (j) Varma, R. S.; Dahiya, R. Synlett 1997, 1245.
41. (k) Varma, R. S.; Dahiya, R.; Kumar, S. Tetrahedron Lett. 1997, 38, 5131.
42. (l) Varma, R. S.; Saini, R. K. Synlett 1997, 857. For oxidation reactions see:
43. (m) Varma, R. S.; Dahiya, R. Tetrahedron Lett. 1997, 38, 2043.
44. (n) Varma, R. S.; Saini, R. K.; Meshram, H. M. Tetrahedron Lett. 1997, 38, 6525.
45. (o) Varma, R. S.; Dahiya, R.; Saini, R. K. Tetrahedron Lett. 1997, 38, 7029.
46. (p) Varma, R. S.; Dahiya, R.; Saini, R. K. Tetrahedron Lett. 1997, 38, 7823.
47. (q) Varma, R. S.; Dahiya, R. Tetrahedron Lett. 1998, 39, 1307.
48. (r) Varma, R. S.; Dahiya, R.; Kumar, D. Molecules Online 1998, 2, 82.
49. (s) Varma, R. S.; Saini, R. K. Tetrahedron Lett. 1998, 39, 1481. For reduction reactions see:
50. (t) Varma, R. S.; Saini, R. K. Tetrahedron Lett. 1997, 38, 4337.
51. (u) Varma, R. S.; Naicker, K. P. Molecules Online 1998, 2, 94.
52. 12. Wade, R. C. J. Mol. Catal. 1983, 18, 273.
53. 13. Pitman, C. U., Jr.; Massry, A. M. El., Amer, A. Synth. Commun. 1990, 20, 1091.
54. 14. Tabaei, S.-M. H.; Pitman, C. U., Jr.; Mead, K. T. Tetrahedron Lett. 1991, 32, 2727.
55. 15. For a critical evaluation of activation process by microwaves see: Raner, K. D.; Strauss, C. R.; Vyskoc, F.; Mokbel, L. J. Org. Chem. 1993, 58, 950. The temperature of the reaction mixture inside the alumina bath (heat sink) in a Sears Kenmore microwave oven equipped with a turntable at full power (900 Watts) reached ∼65 °C after 30 seconds of irradiation as measured by insertion of a thermometer in the alumina bath.
56. 16 Roe, A.; Montgomery, J. A. J. Am. Chem. Soc. 1953, 75, 910.
57. 17 Kawakami, T.; Sugimoto, T.; Shibata, L; Baba, A.; Matsuda, H.; Sonoda, N. J. Org. Chem. 1995, 60, 2677.
58. 18. (a) Ruckdeschel, G.; Stransky, D.; Schonenberger, H. Pharmazie 1976, 31, 374; Chem. Abstr. 1976, 85, 137174j.
59. 18. (a) Ruckdeschel, G.; Stransky, D.; Schonenberger, H. Pharmazie 1976, 31, 374; Chem. Abstr. 1976, 85, 137174j.
60. 19. Beilstein 73(I), 237.
61. 20 Heilbron, I.; Cook, A. H.; Bunbury, H. M.; Hey, D. H., Ed., Dictionary of Organic Compounds, Vol III, Oxford University Press, NY, 1965, pp 1657.
62. 21. Walker, G. N.; Klett, M. A. J. Med. Chem. 1966, 9, 624.
63. 22 Billman, J. H.; Diesing, A. C. J. Org. Chem. 1957, 22, 1068.
64. 23 Beilstein 13, 607.
65. 24. Roberts, R. M.; Hussein, F. A. J. Am. Chem. Soc. 1960, 82, 1950.
66. 25. Graham, S. H.; Williams, A. J. S. Tetrahedron 1965, 21, 3263.
67. 26. Gasc, M. B.; Perie, J.; Lattes, A. Tetrahedron 1978, 34, 1943.
68. 27. Hutchins, R. O.; Su, W.-Y.; Sivakumar, R.; Cistone, F.; Stercho, Y. P. J. Org. Chem. 1983, 48, 3412.
69. 28. Kotsuki, H.; Yoshimura, N.; Kadota, I.; Ushio, Y.; Ochi, M. Synthesis 1990, 401.