Reductive cyclisation in the synthesis of 6-membered N-heterocycles

Current Organic Chemistry

Volumn 8, Issue 16, 2004, Pages 1607-1628

  Tsoungas, Petros G ^a   Diplas, Andreas I ^b  

^a Ministry of Development   (Greece)

^b UNIVERSITY OF PATRAS   (Greece)

Author keywords

[No Author keywords available]

Indexed keywords

SYNTHESIS (CHEMICAL);

HETEROCYCLIC STRUCTURES; N-HETEROCYCLES; N-HETEROCYCLIC; REDUCTIVE CYCLIZATION; SELECTED EXAMPLES;

CYCLIZATION;

2 AMINOQUINOLINE; 2 AZABICYCLO[3,3,1]NONANE DERIVATIVE; ALKALOID; AMIDINE; HETEROCYCLIC COMPOUND; IMIDAZOLE DERIVATIVE; IMIDAZO[4,5 B]PYRIDINE; LACTAM DERIVATIVE; PYRIDAZINE DERIVATIVE; QUINAZOLINE DERIVATIVE; QUINAZOLINONE DERIVATIVE; QUINOLINE DERIVATIVE; QUINOXALINE DERIVATIVE; UNCLASSIFIED DRUG;

CATALYSIS; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; REDUCTION; REVIEW; STRUCTURE ANALYSIS;

EID: 5744230320     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/1385272043369737     Document Type: Review

References (92)

1. Hagan, D. J.; Gimenez-Arnau, E.; Schwalbe, C. H.; Stevens, M. F. G. J. Chem. Soc., Perkin Trans. 1, 1997, 2739.
2. Palacios, F.; Aparicio, D.; Garcia, J. Tetrahedron, 1998, 54, 1647.
3. Kotsuki, H.; Sakai, H.; Morimoto, H.; Suenaga, H. Synlett. 1999, 1993.
4. Cirrincione, G.; Almerico, A. W.; Barraja, P.; Diana, P.; Lauria, A.; Passananti, A.; Musiu, C.; Pani, A.; Murtas, P.; Minnei, C.; Marongiu, M. E.; La Colla, P. J. Med. Chem., 1999, 42, 2561.
5. Seijas, J. A.; Pilar Vazquez-Tato M.; Montserrat Martinez, M. Tetrahedron Lett., 2000, 41, 2215.
6. Zhang, L. -h.; Tan, Z Tetrahedron Lett., 2000, 41, 3025.
7. Besson, T.; Guillard, J.; Rees, C. W. Tetrahedron Lett. 2000, 41, 1027.
8. Comoy, C.; Guérin, V.; Pfeiffer, B.; Reltori, M. C.; Renard, P.; Guillaumet, G. Bioorg. Med. Chem., 2000, 8, 483.
9. Szczepankiewicz, W.; Suwiskj, J.; Bujok, R. Tetrahedron 2001. 56, 9343.
10. Mizuno, T.; Okamoto, N.; Ito, T.; Miyata, T. Tetrahedron Lett., 2000, 41, 1051.
11. Mizuno, T.; Okamoto, N.; Ito, T.; Miyata, T. Heteroat. Chem., 2000, 11, 428.
12. Itoh, T.; Maeda, K.; Wada, T.; Tomimoto, K.; Mase, T. Tetrahedron Lett., 2002, 43, 9287.
13. Dyachenko, V. D.; Tkacheau, R. P. Russ. J. Org. Chem., 2003, 39, 757 and references cited therein.
14. Majumdar, K. C.; Basu, P. K. Heterocycles, 2002, 57, 2413 and references cited therein.
15. Katritzky, A. R.; Rees, C. W. Comprehensive Heterocyclic Synthesis, Academic Press: Oxford, 1984.
16. Katritzky, A. R.; Rees, C. W. Comprehensive Heterocyclic Chemistry II, Academic Press: Oxford, 1996.
17. Katritzky, A. R.; Pozharskii, A. F. Handbook of Heterocyclic Chemistry, 2nd Ed.; Pergamon, 2000.
18. Gilchrist, T. L. Heterocyclic Chemistry, 3rd Ed.; Longman, 1997.
19. Gilchrist, T. L. J. Chem. Soc., Perkin Trans. 1, 2001, 2491 and references cited therein.
20. Weissberger, A.; Taylor, E. C. Chemistry of Heterocyclic Compounds, A Series of Monographs, John Wiley Interscience.
21. Thebtaranonth, C.; Thebtaranonth, Y. Cyclisation Reactions CRC Press: London, 1994.
22. Naito, T.; Tanada, H.; Suzuki, Y.; Saito, H.; Kigushi, T.; Ninomiya, I. Heterocycles, 1993, 36, 2345.
23. McDonald, C. E.; Galka, A. M.; Green, A. I.; Keane, J. M.; Kowalchik, J. E.; Micklitsch, C. M.; Wisnoski, D. D. Tetrahedron Lett. 2001, 42, 163.
24. Chatgilialoglu, C.; Crich, D.; Komatsu, M.; Ryu, I. Chem. Rev., 1999, 99, 1991.
25. Tennant, G.; Wallis, C. J.; Weaver, G. W. J. Chem. Soc., Perkin Trans. 1, 1999, 629.
26. Sakamoto, T.; Kondo, Y.; Uchiyama, D.; Yamanaka, H. Tetrahedron, 1991, 47, 5111.
27. Yang, Y. Synth. Commun., 1989, 19, 1001.
28. Sicker, D. J. Heterocycl. Chem., 1992, 29, 275.
29. Banik, W.; Kim, D. I.; Lee, H. J.; Chung, W. -J.; Kim, B. H.; Lee, S. W. Tetrahedron Lett., 1997, 38, 4579.
30. Banik, W.; Rhee, J. U.; Lee, S. H.; Lee, N. H. Kim, B. H.; Kim, K. S. Tetrahedron Lett., 1995, 36, 2793.
31. Banik, W.; Kim, D. I.; Koo, S.; Rhee, J. U.; Shin, S. S.; Kim, B. H. Tetrahedron Lett., 1997, 38, 845.
32. Boi, C.; de la Fuente, J. M.; Poliakoff, M. New J. Chem. 1999, 23, 641.
33. Zhou, L.; Tu, S.; Shi, D.; Dai, G. J. Chem. Res., 1998, 5, 398.
34. Banik, B. K.; Banik, I.; Hackfeld, L., Becker, F. F. Heterocycles, 2002, 56, 467.
35. Park, K. H.; Joo, H. S.; Kim, S. W., Park, M. S.; Shin, P. S., K Jun,.; Alm, K. II. Tetrahedron Lett., 1999, 40, 1145.
36. Cho, C. S.; Kim, T. K.; Shim, S. C. J. Heterocycl. Chem. 2002, 39, 291.
37. Cho, C. S.; Kim, T. K.; Kim, B. T.; Kim, T. -J.; Shim, S. C. J. Organomet. Chem., 2002, 650, 65.
38. Wang, X.; Zhang, Y. Synth. Commun., 2002, 32 3617.
39. Shi, D.; Zao, H.; Wang, X.; Yao, C., Zhou, L. Synth. Commun., 2002, 32, 3311.
40. Basavaiah, D.; Reddy, R. M.; Kunaragurubaran, N.; Sharada, D. S. Tetrahedron, 2002, 57, 3693.
41. O'Dell, K.; Nicholas, K. M. Tetrahedron, 2003, 59, 747.
42. Familoni, O. B.; Kaye, P. T.; Klaas, P. J. J. Chem. Soc. Chem. Commun., 1998, 2563.
43. Chung, Y. M.; Lee, H. J.; Hwang, S. S.; Kim, J. N. Bull. Kor. Chem. Soc., 2001, 22, 799.
44. Kim, J. N.; Lee, K. Y,; Kim, H. S.; Kim, T. Y. Org. Lett. 2000, 2, 799.
45. Barros, A. I. R. N. A.; Silva, A. M. S. Tetrahedron Lett. 2003, 44, 5893.
46. Kalayanov, G. D.; Choi, J. -K. Heterocycles, 1998 48, 1221.
47. Quirante, J.; Escolano, C.; Costeja, L.; Bonjoch, J. Tetrahedron, 1997, 38, 6901.
48. Quirante, J.; Escolano, C.; Massot, M.; Bonjoch, J. Tetrahedron, 1997, 53, 139.
49. J. Bonjoch, D. Solé and J. Bosch, J. Am. Chem. Soc., 1993, 115, 2064.
50. Solé, D.; Parés, A.; Bonjoch, J. Tetrahedron, 1994, 50, 9769.
51. Bunce, R. A.; Herron, D. M.; Johnson, L. B.; Kotturi, S. V. J. Org. Chem., 2001, 66, 2822.
52. Solé, D.; Garcia-Rubio, S.; Vallverdú, L.; Bonjoch, J. J. Org. Chem., 2001, 66, 5266.
53. Supsana, P.; Tsoungas, P. G.; Varvounis, G. Synthesis, submitted.
54. Gallou-Dagommer, I.; Gastaud, P.; Rajanbabu, T. V. Org. Lett., 2001, 3, 2053.
55. Nakahara, S.; Kubo, A. Heterocycles, 2003, 60 2017.
56. de la Fuente, J. A.; Martin, M. J., del MarBlanco, M.; Pascual-Alfonso, E.; Avendano, C.; Menéendez, J. C. Biorg. Med. Chem., 2001, 9, 1807.
57. Makosza, M.; Wróbel, Z. Heterocycles, 1992, 33, 585.
58. Kawase, M.; Miyake, Y.; Sakamoto, T.; Shimada, M.; Kikugawa, Y. Tetrahedron, 1989, 45, 1635.
59. Guillaume, M.; Janousek, Z.; Viehe, H. G. Synthesis, 1995, 920.
60. Lee, S. G.; Kweon, D. -H.; Yoon, Y. -J. J. Heterocycl. Chem., 2001, 38, 1179.
61. Lee, S. G.; Choi, S. Y.; Yoon, Y. -J. J. Heterocycl. Chem. 1992, 29, 1409.
62. Park, J. W.; Kweon, D. H.; Kang, Y. J.; Lee, W. S.; Clio, S. D.; Yoon, Y. -J. J. Heterocycl. Chem., 2000, 37, 5.
63. Cho, S. D.; Chung, J. W.; Choi, W. Y.; Kim, S. K.; Yoon, Y. J. J. Heterocycl. Chem., 1994, 31, 1199.
64. Miyamoto, T.; Matsumoto, J. -ichi. Chem. Pharm. Bull., 1990, 38, 3211.
65. Ollis, W. D.; Stanforth, S. P.; Ramsden, C. A. Tetrahedron 1985, 41, 2239.
66. Ollis, W. D.; Stanforth, S. P.; Ramsden, C. A. J. Chem. Soc., Perkin Trans. 1, 1989, 961.
67. Tsoungas, P. G.; Diplas, A. I. Curr. Org. Chem., submitted.
68. Chibani, A.; Hazard, R.; Tallec, A. Bull. Soc. Chim. Fr. 1991, 128, 814, Su, W.; Yang, B. Aust. J. Chem., 2002, 55, 695.
69. Akazome, M.; Yamamoto, J.; Kondo, T.; Watanabe, Y. J. Organomet. Chem., 1995, 494, 229.
70. Akazome, M,; Kondo, T.; Watanabe, Y. J. Org. Chem., 1993, 58, 769.
71. CO can effect, when metal-promoted, deoxygenation of nitro compounds [72, 73].
72. Cenini, S.; Ragaim, F. Catalytic Reductive Carbonylation of Organic Nitro Compounds. Kluwer Academic: Dordrecht Netherlands, 1997.
73. Tafesh, A. M.; Weigury, J. Chem. Rev., 1996, 96, 2035.
74. Valderrama, J. A.; Pessoa-Mahana, H.; Sarras, G.; Tapia, R. Heterocycles, 1999, 51, 2193
75. Yu, Y.; Ostresh, J.; Houghten, R. A. J. Org. Chem., 2003, 67, 5831.
76. Kamal, A.; Venkata Ramana, K.; Babu Ankati, H.; Venkata Ramana, A. Tetrahedron Lett., 2002, 43, 6861.
77. Nishiyama, Y.; Hirose, M.; Kitagaito, W.; Sonoda, N. Tetrahedron Lett., 2002, 43, 1855.
78. Barrows, T. H.; Farina, P. R.; Chrzanowski, R. L.; Benkovic, P. A.; Benkovic, S. J. J. Am. Chem. Soc., 1976, 98, 3678.
79. Massacret, M.; Lhoste, P.; Sinou, D. Eur. J. Org. Chem. 1999 129.
80. Alo, B. I.; Avent, A. G.; Hanson, J. R.; Ode, A. E. J. Chem. Soc., Perkin Trans. 1, 1988, 1997.
81. Le Gall, E.; Renaud, T.; Hurvois, J. P.; Tallec, A.; Moinet, C. Synlett., 1998, 513.
82. David, J. Y.; Hurvois, J. P.; Tallec, A.; Toupet, L. Tetrahedron, 1995, 51, 3181.
83. Renaud, T.; Hurvois, J. -P.; Uriac, P. Eur. J. Org. Chem. 2001, 987.
84. Shono, T.; Kise, N.; Shirakawa, E.; Matsumoto, H.; Okazaki, E. J. Org. Chem., 1991, 56, 3063.
85. Pitts, M. R.; Harrison, J. R.; Moody, C. J. J. Chem. Soc., Perkin Trans. 1, 2001, 955.
86. Mercer, G. J.; Sigman, M. S. Org. Lett., 2003, 5, 1591.
87. Krchnák, Szabo, V.; L.; Vágner, J. Tetrahedron Lett. 2000, 41, 2835.
88. Holland, R. J.; Hardeastle, I. R.; Jarman, M. Tetrahedron Lett., 2002, 43, 6435.
89. Andersch, J.; Sicker, D. J. Heterocycl. Chem., 1999 36, 589.
90. Mezheritskii, V. V.; Tkachenko, V. V. Adv. Heterocycl. Chem., 1990, 51, 1 and references cited therein.
91. Tsoungas, P. G. Cazz. Chim. Ital., 1986, 116 405.
92. Pelletier, J. C.; Cava, M. P. J. Org. Chem., 1987 52, 616.