A novel, tandem construction of C-N and C-C bonds: Facile and one-pot transformation of the Baylis-Hillman adducts into 2-benzazepines

Chemical Communications

Volumn 4, Issue 1, 2004, Pages 32-33

  Basavaiah, Deevi ^a   Satyanarayana, Tummanapalli ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; BENZAZEPINE DERIVATIVE; CARBON; NITROGEN;

ARTICLE; BAYLIS HILLMAN REACTION; DRUG SYNTHESIS; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 1642286023     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/b310550d     Document Type: Article

References (56)

1. J. A. May, R. K. Zeidan, B. M. Stoltz: Tetrahedron Lett. 2003 44: 1203
2. C. Guillou, J-L. Beunard, E. Gras, C. Thal: Angew. Chem., Int. Ed. 2001 40: 4745
3. C-K. Sha, A-W. Hong, C-M. Huang: Org. Lett. 2001 3: 2177
4. J. Jin, S. M. Weinreb: J. Am. Chem. Soc. 1997 119: 2050
5. J. M. Boente, L. Castedo, R. Cuadros, J. M. Saa, R. Suau, A. Perales, M. Martinez-Ripoll, J. Fayos: Tetrahedron Lett. 1983 24: 2029
6. R. E. Johnson and C. A. Busacca (Sterling drug, Inc.), US Pat. 5,098,901;
7. R. E. Johnson and C. A. Busacca Chem. Abstr., 1992, 117, 7949j
8. P. Croisier and L. Rodriguez (UCB S. A.), Ger. Offen. 2,733,868 and 2,733,869;
9. P. Croisier and L. RodriguezChem. Abstr., 1978, 88, 152455g and 152456h
10. J. A. Meschino (McNeil Laboratories, Inc.), US Pat. 3,894,072;
11. J. A. MeschinoChem. Abstr., 1975, 83, 114031e
12. J. A. Meschino (McNeil Laboratories, Inc.), US Pat. 3,828,096;
13. J. A. Meschino Chem. Abstr., 1974, 81, 136001f
14. J. A. Meschino (McNeil Laboratories, Inc.), US Pat. 3,483,186;
15. J. A. Meschino Chem. Abstr., 1970, 72, 121383x
16. H. Fujimura and M. Hori (Takeda Chemical Industries, Ltd.), US Pat. 3,409,607;
17. H. Fujimura and M. Hori Chem. Abstr., 1969, 70, 77827c
18. A. Kamimura, Y. Taguchi, Y. Omata, M. Hagihara: J. Org. Chem. 2003 68: 4996
19. M. Nyerges, A. Viranyi, A. Pinter, L. Toke: Tetrahedron Lett. 2003 44: 793
20. J. C. Martins, K. V. Rompaey, G. Wittman, C. Tomboly, G. Toth, N. De Kimpe, D. Tourwe: J. Org. Chem. 2001 66: 2884
21. R. Gamez-Montano, M. I. Chavez, G. Roussi, R. Cruz-Almanza: Tetrahedron Lett. 2001 42: 9
22. L. Ollero, L. Castedo, D. Dominguez: Tetrahedron Lett. 1998 39: 1413
23. A. G. Griesbeck, H. Mauder: Angew. Chem., Int. Ed. Engl. 1992 31: 73
24. R. A. Holton, M. P. Sibi, W. S. Murphy: J. Am. Chem. Soc. 1988 110: 314
25. D. Basavaiah, A. J. Rao: Chem. Commun. 2003 604
26. D. Basavaiah, T. Satyanarayana: Tetrahedron Lett. 2002 43: 4301
27. D. Basavaiah, T. Satyanarayana: Org. Lett. 2001 3: 3619
28. D. Basavaiah, M. Bakthadoss, S. Pandiaraju: Chem. Commun. 1998 1639
29. R. Bishop, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 6, p. 261
30. L. I. Krimen, D. J. Cota: Org. React. 1969 17: 213
31. K. V. Emelen, T. D. Wit, G. J. Hoornaert, F. Compernolle: Org. Lett. 2000 2: 3083
32. K. Hoesch: Ber. Dtsch. Chem. Ges. 1915 48: 1122
33. J. Houben: Ber. Dtsch. Chem. Ges. 1926 59: 2878
34. P.E. Spoerri, A. S. DuBois: Org. React. 1949 5: 387
35. W. Ruske, in Freidel–Crafts and Related Reactions, ed. G. A. Olah, Wiley-Interscience, New York, 1964, vol. III, part I, ch. 32
36. M. Yato, T. Ohwada, K. Shudo: J. Am. Chem. Soc. 1991 113: 691
37. Y. Sato, M. Yato, T. Ohwada, S. Saito, K. Shudo: J. Am. Chem. Soc. 1995 117: 3037
38. R. Kawe-eki, A. P. Mazurek, L. Kozerski, J. K. Maurin: Synthesis 1999 751
39. D. Basavaiah, A. J. Rao, T. Satyanarayana: Chem. Rev. 2003 103: 811
40. E. Ciganek, in Organic Reactions, ed. L. A. Paquette, John Wiley & Sons, New York, 1997, vol 51, p. 201
41. D. Basavaiah, P. Dharma Rao, R. Suguna Hyma: Tetrahedron 1996 52: 8001
42. S. E. Drewes, G. H. P. Roos: Tetrahedron 1988 44: 4653
43. V. K. Aggarwal, I. Emme, S. Y. Fulford: J. Org. Chem. 2003 68: 692
44. K.-S. Yang, W.-D. Lee, J.-F. Pan, K. Chen: J. Org. Chem. 2003 68: 915
45. W. P. Almeida, F. Coelho: Tetrahedron Lett. 2003 44: 937
46. H. Kraiem, M. I. Abdullah, H. Amri: Tetrahedron Lett. 2003 44: 553
47. M. Shi, Y-M. Xu: Angew. Chem., Int. Ed. 2002 41: 4507
48. C. Yu, L. Hu: J. Org. Chem. 2002 67: 219
49. L.-C. Wang, A. L. Luis, K. Agapiou, H.-Y. Jang, M. J. Krische: J. Am. Chem. Soc. 2002 124: 2402
50. S. A. Frank, D. J. Mergott, W. R. Roush: J. Am. Chem. Soc. 2002 124: 2404
51. R. Räcker, K. Döring, O. Reiser: J. Org. Chem. 2000 65: 6932
52. G. Li, J. Gao, X. Wei II, M. Enright: Org. Lett. 2000 2: 617
53. A. G. M. Barrett, A. S. Cook, A. Kamimura: Chem. Commun. 1998 2533
54. D. Basavaiah, P. K. S. Sarma: Chem. Commun. 1992 955
55. D. Basavaiah, M. Krishnamacharyulu, R. Suguna Hyma, S. Pandiaraju: Tetrahedron Lett. 1997 38: 2141
56. H. J. Lee, M. R. Seong, J. N. Kim: Tetrahedron Lett. 1998 39: 6223