Domino carbocationic rearrangement of α-[bis(methylthio)methylene] alkyl-2-(3/2-indolyl) cyclopropyl ketones

Journal of Organic Chemistry

Volumn 72, Issue 4, 2007, Pages 1388-1394

  Yadav, A K ^a   Peruncheralathan, S ^a   Ila, H ^a   Junjappa, H ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

CARBAZOLE DERIVATIVES; LEWIS ACIDS;

AROMATIC COMPOUNDS; INORGANIC ACIDS; OLEFINS; REACTION KINETICS; SUBSTITUTION REACTIONS;

KETONES;

2 INDOLYLCYCLOPROPYL KETONE DERIVATIVE; 3 INDOLYLCYCLOPROPYL KETONE DERIVATIVE; CARBAZOLE DERIVATIVE; CYCLOPROPANE DERIVATIVE; INDOLE DERIVATIVE; KETONE DERIVATIVE; LEWIS ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; ORGANIC CHEMISTRY; STRUCTURE ANALYSIS;

EID: 33846987583     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo062302a     Document Type: Article

References (49)

1. (a) Review: Steyn, P. S.; Vleggaar, R. Fortschr. Chem. Org. Naturust. 1985, 48, 1.
2. (b) Riche, C.; Chiaroni, A.; Dubois, G.; Hocquemiller, R.; Leboeuf, M.; Cave, et A. Planta Med. 1980, 39, 206.
3. (c) Tillequin, F.; Koch, M.; Bert, M.; Sevenet, T. J. Nat. Prod. 1979, 42, 92.
4. (d) Achenbach, H.; Biemann, K. J. Am. Chem. Soc. 1965, 87, 4944.
5. (a) Smith, A. B., III; Mewshaw, R. J. Am. Chem. Soc. 1985, 107, 1769.
6. (b) Mewshaw. R. E.; Taylor, M. D.; Smith, A. B., III. J. Org. Chem. 1989, 54, 3449.
7. (c) Smith, A. B., III; Leenay, T. L. J. Am. Chem. Soc. 1989, 111, 5761.
8. Kong, Y-C.; Cheng, K-F.; Cambie, R. C.; Waterman, P. G, J. Chem. Soc. Chem. Commun. 1985, 47.
9. (a) Kong, Y-C.; Ng, K-H.; Wat, K-H.; Wong, A.; Saxena, I. F.; Cheng, K-F.; But, P. P.; Chang, H-T. Planta Med. 1985, 4, 304.
10. (b) Wong, D. C. C.; Fong, W. P.; Lee, S. S. T.; Kong, Y-C.; Cheng, K. F.; Stone, G. Eur. J. Pharmacol. 1998, 362, 87.
11. (c) Cheng, K. F.; Wong, T. T.; Chan, K. P.; Kong, Y. C. Eur. J. Med. Chem .1992, 27, 121.
12. (d) Leung, T. W. T.; Cheng, G.; Chui, C. H.; Ho, S. K. W.; Lau, F. Y.; Tjong, J. K. J.; Poon, T. C. C; Tang, J. C. O; Tse, W. C. P.; Cheng, K. F.; Kong, Y. C. Chemotherapy 2000, 46, 62.
13. Campos, K. R.; Journet, M.; Lee, S.; Grabowski, E. J. J.; Tillyer, R. D. J. Org. Chem. 2005, 70, 268.
14. Tsuri, T.; Honma, T.; Hiramatsu, Y.; Okada, T.; Mitsumori, S.; Inagaki, M.; Arimura, A.; Yasui, K.; Asanuma, F.; Kishino, J.; Ohtani, M. J. Med. Chem. 1997, 40, 3504.
15. (a) Ishikura, M.; Imaizumi, K.; Katagiri, N. Heterocycles 2000, 53, 2201 and references therein.
16. (b) Sheu, J-H.; Chen, C-A.; Chen, B-H. Chem. Commun. 1999, 203.
17. (c) Henry, K. J., Jr.; Grieco, P. A. J. Chem. Soc. Chem. Commun. 1993, 510.
18. (d) Cheng, K- F.; Chan, K-P.; Kong, Y-C.; Ho, D-D. J. Chem. Soc. Perkin Trans. 1 1991, 2955.
19. (e) Wenkert, E.; Moeller, P. D. R.; Piettre, S. R.; McPhail, A. T. J. Org. Chem. 1988, 53, 3170.
20. (f) Kutney, J. P.; Lopez, F. J.; Huang, S. P.; Kurobe, H.; Flogaus, R.; Piotrowska, K.; Rettig, S. J. Can. J. Chem. 1991, 69, 949.
21. (a) England, D. B.; Kuss, T. D. O.; Keddy, R. G.; Kerr, M. A. J. Org. Chem. 2001, 66, 4704.
22. (b) Harrison, C-A.; Leineweber, R.; Moody, C. J.; Williams, J. M. J. Tetrahedron Lett. 1993, 34, 8527.
23. (c) Bergman, J.; Venemalm, L. Tetrahedron 1992, 48, 759.
24. (d) Bergman, J.; Venemalm, L.; Gogoll, A. Tetrahedron 1990, 46, 6067.
25. (e) Bergman, J.; Venemalm, L. Pure Appl. Chem. 1994, 66, 2331.
26. (f) Martinez, S. J.; Dalton, L.; Joule, J. A. Tetrahedron 1984, 40, 3339.
27. (g) Miyata, O.; Kimura, Y.; Naito, T. Chem. Commun. 1999, 2429.
28. (h) Ganesan, A.; Heathcock, C. H. Tetrahedron Lett. 1993, 34, 439.
29. (a) Chakrabarti, S.; Panda, K.; Ila, H.; Junjappa, H. Synlett 2005, 309.
30. (b) Sundaram, G. S. M.; Venkatesh, C.; Syam, Kumar, U. K.; Ila, H.; Junjappa, H. J. Org. Chem. 2004, 69, 5760.
31. (c) Venkatesh, C.; Ila, H.; Junjappa, H.; Mathur, S.; Huch, V. J. Org. Chem. 2002, 67, 9477.
32. (d) Syam Kumar, U. K.; Ila, H.; Junjappa, H. Org. Lett. 2001, 3, 4193.
33. (e) Review: Ila, H.; Junjappa, H.; Mohanta, P. K. Progress in Heterocyclic Chemistry; Gribble, G. W., Gilchrist, T. L., Eds.; Pergamon: New York, 2001; Vol. 13. Chapter 1, p 1 and references therein.
34. (a) Deb, B.; Asokan, C. V.; Ila, H.; Junjappa, H. Tetrahedron Lett. 1988, 29, 2111.
35. (b) Deb. B.; Ila, H.; Junjappa, H. J. Chem. Res. (synop.) 1990, 356.
36. J. Chem. Res. (miniprint) 1990, 2728.
37. (c) Patro, B.; Deb, B;, Ila, H.; Junjappa, H. J. Org. Chem. 1992, 57, 2257.
38. (d) Patro, B.; Deb, B.; Ila, H.; Junjappa, H. Tetrahedron 1994, 50, 255.
39. (a) Patra, P. K.; Patro, B.; Ila, H.; Junjappa, H. Tetrahedron Lett. 1993, 34, 3951.
40. (b) Patra, P. K.; Sriram, V.; Ila, H.; Junjappa, H. Tetrahedron 1998, 54, 531.
41. (c) Syam Kumar, U. K.; Patra, P. K.; Ila, H.; Junjappa, H. J. Chem. Soc. Perkin Trans. 1 2000, 1547.
42. (a) Mohanta, P. K.; Peruncheralathan, S.; Ila, H.; Junjappa, H. J. Org. Chem. 2001, 66, 1503.
43. (b) Nandi, S.; Syam, Kumar, U. K.; Ila, H.; Junjappa, H. J. Org. Chem. 2002, 67, 4916.
44. (c) Peruncheralathan, S.; Sriram, V.; Ila, H.; Junjappa, H. Tetrahedron 2004, 60, 5603.
45. (a) Thuillier, A.; Vialle, J. Bull. Soc. Chim. Fr. 1962, 2182.
46. (b) Asokan, C. V.; Ila, H.; Junjappa, H. Synthesis 1985, 163.
47. Chen, P.; Barrish, J. C.; Iwanowicz, E.; Lin, J.; Bednarz, M. S.; Chen, B.-C. Tetrahedron Lett. 2001, 42, 4293.
48. The similar product, i.e., 1-[bis(methylthio)ethylidene]-N- methylcarbazole 29 could not be isolated from 3-indolylcyclopropyl ketone 2b, probably because of steric crowding. (Chemical Equation Presented)
49. Randall, L. O.; Baruth, H. Arch. Int. Pharmacodyn. Ther. 1976, 220 (1), 94.