(PhO)3P·Cl2-promoted bischler-napieralski-type cyclization: A mild access to β-carbolines

Synlett

Volumn , Issue 4, 2005, Pages 661-663

  Spaggiari, Alberto ^a   Davoli, Paolo ^a   Blaszczak, Larry C ^b   Prati, Fabio ^a  

^a UNIVERSITY OF MODENA AND REGGIO EMILIA   (Italy)

^b ELI LILLY AND COMPANY   (United States)

Author keywords

Alkaloids; Bischler napieralski cyclizations; Chlorine; Indoles; Triphenyl phosphite

Indexed keywords

BETA CARBOLINE DERIVATIVE; CHLORINE DERIVATIVE; DICHLOROMETHANE; PHOSPHITE; PHOSPHORUS DERIVATIVE;

ARTICLE; BISHCLER NAPIERALSKI CYCLIZATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHROMATOGRAPHY; CYCLIZATION; POLYMERIZATION; PURIFICATION; TEMPERATURE DEPENDENCE;

EID: 15444377964     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-862394     Document Type: Article

References (38)

1. Spaggiari, A.; Blaszczak, L. C.; Prati, F. Org. Lett. 2004, 6, 3885.
2. (a) Hatfield, L. D.; Blaszczak, L. C.; Fisher, J. W. US Patent 4,230,644, 1980; Chem. Abstr. 1981, 94, 156523.
3. (b) Hatfield, L. D.; Blaszczak, L. C.; Fisher, J. W. US Patent 4,226,986, 1980; Chem. Abstr. 1981, 94, 103348.
4. (a) Coe, D. G.; Landauer, S. R.; Rydon, H. N. J. Chem. Soc. 1954, 2281.
5. (b) Rydon, H. N.; Tonge, B. L. J. Chem. Soc. 1956, 3043.
6. Tseng, C. K. J. Org. Chem. 1979, 44, 2793.
7. (a) Schultes, R. E.; Hofmann, A. The Botany and Chemistry of Hallucinogens; Charles C. Thomas Publisher: Springfield, 1980.
8. (b) Freedland, C. S.; Mansbach, R. S. Drug and Alcohol Dependence 1999, 54, 183.
9. Ott, J. J. Psychoact. Drugs 1999, 31, 171.
10. Airaksinen, M. M.; Kari, I. Med. Biol. 1981, 59, 21.
11. (e) Airaksinen, M. M.; Kari, I. Med. Biol. 1981, 59, 190.
12. Bischler, A.; Napieralski, B. Ber. 1893, 26, 1903.
13. For an excellent review, see: Love, B. Org. Prep. Proced. Int. 1996, 28, 1.
14. Fodor, G.; Gal, J.; Phillips, B. A. Angew. Chem., Int. Ed. Engl. 1972, 11, 919.
15. (a) Nicoletti, M.; O'Hagan, D.; Slawin, A. M. Z. J. Chem. Soc., Perkin Trans. 1 2002, 116.
16. (b) Doi, S.; Shirai, N.; Sato, Y. J. Chem. Soc., Perkin Trans. 1 1997, 2217.
17. (a) Huang, W. J.; Singh, O. V.; Chen, C. H.; Lee, S. S. Helv. Chim. Acta 2004, 87, 167.
18. (b) Wang, Y. C.; Georghiou, P. E. Org. Lett. 2002, 4, 2675.
19. Fujii, T.; Ohba, M.; Ohashi, T. Tetrahedron 1993, 49, 1879.
20. Hino, T.; Lai, Z.; Seki, H.; Kara, R.; Kuramochi, T.; Nakagawa, M. Chem. Pharm. Bull. 1989, 37, 2596.
21. (e) Whaley, W. M.; Govindachari, T. R. Org. React. 1951, 6, 74.
22. Tsuda, Y.; Kimiaki, I.; Toda, J.; Taga, J. Heterocycles 1976, 5, 157.
23. Itoh, N.; Sugasawa, S. Tetrahedron 1957, 1, 45.
24. Snyder, H. R.; Werber, F. X. J. Am. Chem. Soc. 1950, 72, 2962.
25. (a) Kanaoka, Y.; Sato, E.; Yonemitsu, O.; Ban, Y. Tetrahedron Lett. 1964, 35, 2419.
26. (b) Kanaoka, Y.; Sato, E.; Ban, Y. Chem. Pharm. Bull. 1967, 15, 101.
27. Kende, A. S.; Ebetino, F. H.; Battista, R.; Boatman, R. J.; Lorah, D. P.; Lodge, E. Heterocycles 1984, 27, 91.
28. Banwell, M. G.; Bissett, B. D.; Busato, S.; Cowden, C. J.; Hockless, D. C. R.; Holman, J. W.; Read, R. W.; Wu, A. W. J. Chem. Soc., Chem. Commun. 1995, 2551.
29. Larsen, R. D.; Reamer, R. A.; Corley, E. G.; Davis, P.; Grabowski, E. J. J.; Reider, P. J.; Shinkai, I. J. Org. Chem. 1991, 56, 6034.
30. Chern, M. S.; Shih, Y. K.; Dewang, P. M.; Li, W. R. J. Comb. Chem. 2004, 6, 855.
31. 4 and evaporated in vacuo, to provide a thick foam which was triturated with light petroleum, thus affording the desired arnide as a reddish-brown fine powder (70-92% yield).
32. 2 from the action of adventitious HCl, which is reported to enhance its degradation into an inactive form. For more detailed mechanistic insights, see Ref. 1,2a.
33. (a) Späth, E.; Lederer, E. Ber. 1930, 63, 120.
34. (b) Rommelspacher, H.; Brüning, G.; Susilo, R.; Nick, M.; Hill, R. Eur. J. Pharmacol. 1985, 109, 363.
35. Steglich, W.; Kopanski, L.; Wolf, M.; Moser, M.; Tegtmeyer, G. Tetrahedron Lett. 1984, 25, 2341.
36. (a) Wasson, R. G. Soma, Divine Mushroom of Immortality; Harcourt, Brace and Jovanovich: New York, 1968.
37. (b) Wasson, R. G.; Kramrisch, S.; Ott, J.; Ruck, C. A. P. Persephone's Quest - Entheogens and the Origins of Religion; Yale University Press: New Haven, 1986.
38. Application of Banwell's method14 to substrate 1b failed to give the expected β-carboline 2b.