Indium trichIoride (InCl3)catalyzed imino Diels-Alder reactions: An efficient synthesis of cyclopentaquinolines, azabicyclooctanones and azabicyclononanones

Tetrahedron

Volumn 54, Issue 8, 1998, Pages 1627-1638

  Babu, Govindarajulu ^a   Perumal, Paramasivan T ^a  

^a CENTRAL LEATHER RESEARCH INSTITUTE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

2 CYCLOHEXENONE; AZABICYCLONONANONE DERIVATIVE; AZABICYCLOOCTANONE DERIVATIVE; CYCLOHEPTEN 2 ONE; CYCLOPENTADIENE DERIVATIVE; CYCLOPENTAQUINOLINE DERIVATIVE; INDIUM CHLORIDE; REAGENT; SCHIFF BASE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CONTROLLED STUDY; PRIORITY JOURNAL; SYNTHESIS;

EID: 0032546063     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10370-2     Document Type: Article

References (39)

1. 1. A part of this work has already been published as a preliminary communication. Babu, G.; Perumal, P. T. Tetrahedron Lett., 1997, 38, 5025.
2. 2. a) Weinreb, S. M. in Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I. Pergamon Press: Oxford, 1991, Vol. 5, p. 401.
3. b) Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis, Academic Press: New York, 1987, Chaps. 2 and 9.
4. 3. a) Lin, Y. M.; Oh, T. Tetrahedron Lett. 1997, 38, 727.
5. b) Coz, L. L.; Veyrat-Martin, C.; Wartski, L.; Seyden-Penne, J.; Bois, C.; Philoche-Levisalles, M. J. Org. Chem. 1990, 55, 4870.
6. c) Maggini, M.; Prato, M.; Scorrano, G. Tetrahedron Lett. 1990, 31, 6243.
7. 4. a) Grieco, P. A.; Bahsas, A. Tetrahedron Lett. 1988, 29, 5855.
8. b) Borrione, B.; Prato, M., Scorrano, G.; Stivanello, M. J. Chem. Soc., Perkin Trans. 1, 1989, 2245.
9. c) Gregoire, P. J.; Mellor, J. M.; Merriman, G. D. Tetrahedron Lett. 1991, 32, 7099.
10. d) Mellor, J. M., Merriman, G. D.; Riviere, P. Tetrahedron Lett. 1991, 32, 7103.
11. 5. a) Linkert, F.; Laschat, S.; Kotila, S.; Fox, T. Tetrahedron 1996, 52, 955.
12. b) Linken, F.; Laschat, S.; Knickmeier, M. Liebigs Ann. Chem. 1995, 985.
13. c) Linkert, F.; Laschat, S. Synlett. 1994, 125.
14. d) Lease, T. G.; Shea, K. J. J. Am. Chem. Soc. 1993, 115, 2248.
15. e) Barleunga, J.; Tomas, M.; Ballesteros, A.; Gotor, V. J. Chem. Soc., Chem. Commun. 1989, 267.
16. 6. a) Lucchini, V.; Prato, M.; Scorrano, G.; Tecilla, P. J. Org. Chem. 1988, 53, 2251.
17. b) Lucchini, V.; Prato, M.; Scorrano, G.; Tecilla, P. J. Heterocyclic Chem. 1986, 23, 1153.
18. c) Lucchini, V.; Prato, M.; Quintily, V.; Scorrano, G. J. Chem. Soc., Chem. Commun. 1984, 48.
19. 7. a) Kobayashi, S.; Araki, M., Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett. 1995, 233.
20. b) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synthesis 1995, 1195.
21. c) Kobayashi, S.; Ishitani, H.; Nagayama, S. Chem. Lett. 1995, 423.
22. 8. Zulotukhin, M. A.; Sedova, E. A.; Sorokina, Yu, L.; Salazkin, S. N.; Sangalov, Yu. A.; Sultanova, V. S.; Panasenko, A. A.; Khalivov, L. M.; Muslukhov, R. M. Makromol. Chem. 1990, 191, 1477.
23. 9. Zhun, V. I.; Tsvetkov, A. L.; Sukhikh, A. S.; Sheludyakov, V. D. Zh. Obshch. Khim. 1990, 60, 1104 (Russ); Chem. Abst. 1990, 113, 212074d.
24. 9. Zhun, V. I.; Tsvetkov, A. L.; Sukhikh, A. S.; Sheludyakov, V. D. Zh. Obshch. Khim. 1990, 60, 1104 (Russ); Chem. Abst. 1990, 113, 212074d.
25. 10. Mukaiyama, T.; Ohno, T.; Nishimura, T.; Han, J. S.; Kobayashi, S. Bull. Chem. Soc. Jpn. 1991, 64, 2524.
26. 11. Mukaiyama, T.; Ohno, T.; Nishimura, T.; Suda, S.; Kobayashi, S. Chem. Lett. 1991, 1059.
27. 12. Ohnishi, R.; Suzuki, I.; Ichikawa, M. Chem. Lett. 1991, 841.
28. 13. Mukaiyama, T.; Ohno, T.; Han, J. S.; Kobayashi, S. Chem. Lett. 1991, 949.
29. 14. Loh, T. -P.; Pie, J.; Cao, G. -Q. Chem. Commun. 1996, 1819.
30. 15. Loh, T. -P.; Pie, J.; Lin, M. Chem. Commun. 1996, 2315.
31. 16. Roe, A.; Montgomery, J. A. J. Am. Chem. Soc. 1953, 75, 910.
32. 17. Fringuelli, F.; Minuti, L.; Radics, L.; Taticchi, A.; Wenkert, E. J. Org. Chem. 1988, 53, 4607.
33. 18. Fringuelli, F.; Taticchi, A. Org. Prep. Proc. Int. 1989, 139.
34. 19. Babu, G.; Sridar, V.; Ind. J. Chem. Sect. B. 1996, 35B, 711.
35. 20. Garbisch, E. W. Jr. J. Org. Chem. 1965, 30, 2109.
36. 21. Krishna, R.; Velmurugan, D.; Babu, G.; Perumal, P. T. (Manuscript under preparation).
37. 22. a) Holmes, A. B.; Thompson, J.; Baxter, A. J. G., Dixon, J. J. Chem. Soc., Chem. Commun. 1985, 37.
38. b) Birkinshaw, T. N.; Tabor, A. B.; Holmes, A. B.; Kaye, P.; Mayne, P. M.; Raithby, P. R. J. Chem. Soc., Chem. Commun. 1988, 1599.
39. c) Birkinshaw, T. N.; Tabor, A. B.; Holmes, A. B.; Raithby, P. R. J. Chem. Soc., Chem. Commun. 1988, 1601.