A versatile one-pot synthesis of β-carbolines by reaction of pyranoindolones with phenyl- and benzoylhydrazine

Synthesis

Volumn , Issue 20, 2008, Pages 3273-3278

  Livadiotou, Despina ^a   Hatzimimikou, Dimitra ^a   Neochoritis, Constantinos ^a   Terzidis, Michael A ^a   Tsoleridis, Constantinos A ^a   Stephanidou Stephanatou, Julia ^a  

^a ARISTOTLE UNIVERSITY OF THESSALONIKI   (Greece)

Author keywords

Benzoylhydrazine; Bisnucleophiles; One pot reaction; p Benzylic coupling; Phenylhydrazine; Pyranoindoles

Indexed keywords

AMINES; KETONES;

BENZOYLHYDRAZINE; BISNUCLEOPHILES; ONE-POT REACTION; P-BENZYLIC COUPLING; PHENYLHYDRAZINE; PYRANOINDOLES;

NUCLEAR MAGNETIC RESONANCE;

2 (BENZOYLAMINO) 9 METHYL 1 PROPYL 2,9 DIHYDRO 3H BETA CARBOLIN 3 ONE; 2 (BENZYLAMINO) 1 ETHYL 2,9 DIHYDRO 3H BETA CARBOLIN 3 ONE; 2 (BENZYLAMINO) 1 ETHYL 9 METHYL 2,9 DIHYDRO 3H BETA CARBOLIN 3 ONE; 2 (BENZYLAMINO) 1 METHYL 2,9 DIHYDRO 3H BETA CARBOLIN 3 ONE; 2 (BENZYLAMINO) 1 PROPYL 2,9 DIHYDRO 3H BETA CARBOLIN 3 ONE; 2 9BENZYLAMINO) 1,9 DIMETHYL 2,9 DIHYDRO 3H BETA CARBOLIN 3 ONE; 2 ANILINO 1 ETHYL 2,9 DIHYDRO 3H BETA CARBOLIN 3 ONE; 2 ANILINO 1 ETHYL 9 METHYL 2,9 DIHYDRO 3H BETA CARBOLIN 3 ONE; 2 ANILINO 1 METHYL 2,9 DIHYDRO 3H BETA CARBOLIN 3 ONE; 2 ANILINO 1 PROPYL 2,9 DIHYDRO 3H BETA CARBOLIN 3 ONE; 2 ANILINO 1,9 DIMETHYL 2,9 DIHYDRO 3H BETA CARBOLIN 3 ONE; 2 ANILINO 9 METHYL 1 PROPYL 2,9 DIHYDRO 3H BETA CARBOLIN 3 ONE; BETA CARBOLINE; HYDRAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ONE POT SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 55349095812     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-0028-1083152     Document Type: Article

References (34)

1. Allen, J. R. F.; Holmstedt, B. Phytochemistry 1980, 19, 1573.
2. (a) Love, B. E. Org. Prep. Proced. Int. 1996, 28, 3.
3. (b) Magnier, E.; Langlois, Y. Tetrahedron 1998, 54, 6201.
4. (c) Nakagawa, M. J. Heterocycl. Chem. 2000, 37, 567.
5. (d) Cox, E. D.; Diaz-Arauzo, H.; Huang, Q.; Reddy, M. S.; Ma, C.; Harris, B.; McKernan, R.; Skolnick, P.; Cook, J. M. J. Med. Chem. 1998, 41, 2537.
6. (e) Batch, A.; Dodd, R. H. J. Org. Chem. 1998, 63, 872.
7. (a) Rommelspacher, H.; May, T.; Salewsky, B. Eur. J. Pharmacol. 1994, 252, 51.
8. (b) Kim, H.; Sablin, S. O.; Ramsay, R. R. Arch. Biochem. Biophys. 1997, 337, 137.
9. (c) Herraiz, T.; Chaparro, C. Biochem. Biophys. Res. Commun. 2005, 326, 378.
10. (d) Evans, A. K.; Lowry, C. A. CNS Drug Rev. 2007, 13, 475.
11. (a) Taira, Z.; Kanzawa, S.; Dohara, C.; Ishida, S.; Matsumoto, M.; Sakiya, Y. Jpn. J. Toxicol. Environ. Health 1997, 43, 83.
12. (b) Balón, M.; Muñoz, M. A.; Carmora, C.; Guardado, P.; Galán, M. Biophys. Chem. 1999, 80, 41.
13. Funayama, Y.; Nishio, K.; Wakabayashi, K.; Nagao, M.; Shimoi, K.; Ohira, T.; Hasegawa, S.; Saijo, N. Mutat. Res. 1996, 349, 183.
14. (a) Cox, E. D.; Cook, J. M. Chem. Rev. 1995, 95, 1797.
15. (b) Yu, S.; Berner, O. M.; Cook, J. M. J. Am. Chem. Soc. 2000, 122, 7827.
16. (c) Danieli, B.; Giovanelli, P.; Lesma, G.; Passarella, D.; Saccetti, A.; Silvani, A. J. Comb. Chem. 2005, 7, 458.
17. Loew, G. H.; Nienow, J.; Lawson, J. A.; Toll, L.; Uyeno, E. T. Mol. Pharmacol. 1985, 28, 17.
18. Barbaccia, M. L.; Ravizza, L.; Costa, E. J. Pharmacol. Exp. Ther. 1986, 236, 307.
19. Fuller, R. W.; Wong, C. J.; Hemrick-Luecke, S. K. Life Sci. 1986, 38, 409.
20. (a) Pohl, B.; Luchterhandt, T.; Bracher, F. Synth. Commun. 2007, 37, 1273.
21. (b) Lingam, Y.; Rao, D. M.; Bhowmik, D. R.; Islam, A. Synth. Commun. 2007, 37, 4313.
22. Teshigawara, T. JP42008628, 1967;
23. Chem. Abstr. 1968, 68, 49580g.
24. Plieninger, H.; Müller, W.; Weinerth, K. Chem. Ber. 1964, 97, 667.
25. Dorofeenko, G. N.; Korobkova, V. G.; Guzhina, E. A. Chem. Heterocycl. Compd. 1971, 7, 319.
26. (a) Tolkunov, S. V.; Tolkunov, V. S.; Dulenko, V. I. Chem. Heterocycl. Compd. 2004, 40, 481.
27. (b) Tolkunov, V. S.; Vysotsky, Y. B.; Gorban, O. A.; Shishkina, S. V.; Shishkin, O. V.; Dulenko, V. I. Chem. Heterocycl. Compd. 2005, 41, 515.
28. Katritzky, A. R.; Shcherbakova, I. V. J. Heterocycl. Chem. 1996, 33, 2031.
29. Doitsides, N.; Mentzafos, D.; Mitkidou, S.; Terzis, A.; Stephanidou-Stephanatou, J. Synth. Commun. 1995, 25, 1411.
30. Modi, S. P.; Archer, S. J. Org. Chem. 1989, 54, 5189.
31. Hatzimimikou, D.; Livadiotou, D.; Tsoleridis, C. A.; Stephanidou- Stephanatou, J. Synlett 2008, 1773.
32. (a) Diels, O.; Köllisch, A. Chem. Ber. 1911, 44, 266.
33. (b) Bennasar, M.-L.; Juan, C.; Roca, T.; Monerris, M.; Bosch, J. Tetrahedron 2001, 57, 10125.
34. 2 substituent, have been confirmed after simulation with program Spin Works, version 2.5, available from ftp:// davinci.chem.umanitoba.ca.