Microwave-enhanced Fischer reaction: An efficient one-pot synthesis of γ-carbolines

Synlett

Volumn , Issue 1, 2008, Pages 0077-0082

  Chen, Jing ^a   Chen, Weiliang ^a   Hu, Yongzhou ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

carbolines; Arylhydrazine hydrochloride; Fischer reaction; Microwave irradiation; N acetyl 3 bromo 4 piperidone hydrobromide

Indexed keywords

BROMINE DERIVATIVE; GAMMA CARBOLINE DERIVATIVE; N ACETYL 3 BROMO 4 PIPERIDONE HYDROBROMIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; MICROWAVE RADIATION; ONE POT SYNTHESIS; THERMAL ANALYSIS;

EID: 38549164636     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-992411     Document Type: Article

References (30)

1. (a) Grellier, P.; Ramiaramanana, L.; Millerioux, V.; Deharo, E.; Schrével, J.; Frappier, F.; Trigalo, F.; Bodo, B.; Pousset, J.-L. Phytotherapy Res. 1996, 10, 317.
2. (b) Kirby, G. C.; Paine, A.; Warhurst, D. C.; Noamese, B. K.; Phillipson, J. D. Phytotherapy Res. 1995, 9, 359.
3. (c) Cimanga, K.; De Bruyne, T.; Pieters, L.; Vlietinck, A.; Turger, C. A. J. Nat. Prod. 1997, 60, 688.
4. Acramone, F.; Penco, S. Antitumor Natural Products; Takeuchi, T.; Nitta, K.; Tanaka, N., Eds.; Japan Scientific Press: Tokyo, 1989, 1.
5. (a) Nguyen, C. H.; Lavelle, F.; Riou, J. F.; Bissery, M. C.; Huel, C.; Bisagni, E. Anticancer Drug Des. 1992, 7, 235.
6. (b) Nguyen, C. H.; Bisagni, E.; Lavelle, F.; Bissery, M. C.; Huel, C. Anticancer Drug Des. 1992, 7, 219.
7. Molina, A.; Vaquero, J. J.; Garcia-Navio, J. L.; Alvarez-Builla, J.; Pascual-Teresa, B.; Gago, F.; Rodrigo, M. M.; Ballesteros, M. J. Org. Chem. 1996, 61, 5587.
8. Robinson, R.; Thornley, S. J. Chem. Soc. 1924, 125, 2169.
9. (a) Nantka-Namirski, P.; Zieleniak, J. Acta Poloniae Pharmaceutica 1961, 18, 449.
10. (b) Nantka-Namirski, P.; Zieleniak, J. Acta Poloniae Pharmaceutica 1962, 19, 229.
11. (c) Nantka-Namirski, P.; Zieleniak, J. Acta Poloniae Pharmaceutica 1977, 34, 349.
12. (d) Nantka-Namirski, P.; Zieleniak, J. Acta Poloniae Pharmaceutica 1977, 34, 449.
13. (e) Nantka-Namirski, P.; Zieleniak, J. Acta Poloniae Pharmaceutica 1977, 34, 455.
14. (f) Kermack, W. O.; Storey, N. E. J. Chem. Soc. 1950, 607.
15. (a) Bremer, O. Ann. Chem. 1934, 514, 279.
16. (b) Nantka-Namirski, P.; Zieleniak, J. Acta Poloniae Pharmaceutica 1961, 18, 391.
17. Molina, A.; Vaquero, J. J.; García-Navio, J. L.; Alvarez-Builla, J. Tetrahedron Lett. 1993, 34, 2673.
18. Clark, V. M.; Cox, A.; Herbert, E. J. J. Chem. Soc. 1968, 831.
19. (a) Rocca, P.; Marsais, F.; Godard, A.; Queguiner, G. Tetrahedron 1993, 49, 49.
20. (b) Lwaki, T.; Yasuhara, A.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1 1999, 1505.
21. (a) Robinson, B. Chem. Rev. 1969, 69, 227.
22. (b) Robinson, B. The Fischer Indole Synthesis; Wiley: New York, 1983.
23. Mann, F. G.; Prior, A. F.; Willcox, T. J. J. Chem. Soc. 1959, 3830.
24. Hu, Y. Z.; Chen, Y. Q. Synlett 2005, 42.
25. Lidström, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225.
26. Carlin, R. B.; Larson, G. W. J. Am. Chem. Soc. 1957, 79, 934.
27. 3·OEt. The test tube was placed in the microwave cavity (Initiator™ 2.0, Biotage, 400 W, 2450 MHz) and subjected to microwave irradiation at 230°C for 5 min. After completion of the reaction, the tube was removed and cooled to r.t. The following workup and purification of the crude product was quite the same as above.
28. 2: C, 65.20; H, 3.48; N, 13.82. Found: C, 65.25; H, 3.25; N, 13.89.
29. (a) Ishikawa, M.; Koike, H. JP 10147571, 1998.
30. (b) Sundeen, J. E.; Dejneka, T. US 4122083, 1978.