An efficient route for the synthesis of 2-arylthiazino[5,6-b]indole derivatives

Tetrahedron

Volumn 63, Issue 23, 2007, Pages 4983-4989

  Csomós, Péter ^a,b   Fodor, Lajos ^a,b   Mándity, István ^a   Bernáth, Gábor ^a  

^a UNIVERSITY OF SZEGED   (Hungary)

^b Department of Pediatrics   (Hungary)

Author keywords

2 Aminomethylindole; Hugerschoff reaction; Thiazino 5,6 b indole; Thioamide

Indexed keywords

2 (4 CHLOROTHIOBENZOYLAMINOMETHYL)INDOLE; 2 (4 FLUROTHIOBENZOYLAMINOMETHYL)INDOLE; 2 (4 METHYLTHIOBENZOYLAMINOMETHYL)INDOLE; 2 (THIOBENZOYLAMINOMETHYL)INDOLE; 2 AMINOMETHYLINDOLE; 2 ARYLTHIAZINO{5,6 B]INDOLE DERIVATIVE; 2 THIOBENZAMIDOMETHYLINDOLE DERIVATIVE; 4,5 DIHYDRO 2 (4 CHLOROPHENYL) 1,3 THIAZINO[5,6 B]INDOLE; 4,5 DIHYDRO 2 (4 FLUOROPHENYL 1,3 THIAZINO[5,6 B]INDOLE; 4,5 DIHYDRO 2 (4 METHYLPHENYL 1,3 THIAZINO[5,6 B]INDOLE; 4,5 DIHYDRO 2 PHENYL 1,3 THIAZINO[5,6 B]INDOLE; BENZALDEHYDE; BENZOYL CHLORIDE DERIVATIVE; CHLORIDE; INDOLE DERIVATIVE; PHENYLTRIMETHYLAMMONIUM TRIBROMIDE; THIOAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; PRIORITY JOURNAL; SYNTHESIS;

EID: 34247590208     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.03.132     Document Type: Article

References (32)

1. Sundberg R.J. Indoles (1996), Academic, London
2. Pedras M.S.C., Jha M., and Ahiahonu P.W.K. Curr. Org. Chem. 7 (2003) 1635-1647
3. Takasugi M., Katsui N., and Shirata A. J. Chem. Soc., Chem. Commun. (1986) 1077-1079
4. Dixon R.A., and Lamb C.J. Ann. Rev. Plant Physiol. Plant Mol. Biol. 41 (1990) 339-367
5. Metha R.G., Liu J., Constantinou A., Thomas C.F., Hawthorne M., You M., Gerhäuser C., Pezutto J.M., Moon R.C., and Moriarty M.R. Carcinogenesis 16 (1995) 399-404
6. Kutschy P., Suchý M., Adreani A., Dzurilla M., Kováčik V., Alföldi J., Rossi M., and Gramatová M. Tetrahedron 58 (2002) 9029-9039
7. Csomós P., Fodor L., Sohár P., and Bernáth G. Tetrahedron 61 (2005) 9257-9262
8. Velezheva V.S., Yarosl A.V., Kozik T.A., and Suvorov U.N. Khim. Geterofsikl. Soedin. (1978) 1497-1503
9. Chem. Abstr. 90 (1979) 87375f
10. Romeo G., Russo F., Guccione S., Chabin R., Kuo D., and Knight W.B. Bioorg. Med. Chem. Lett. 4 (1994) 2399-2404
11. Pedras M.S.C., Suchy M., and Ahiahonu P.W.K. Org. Biomol. Chem. 4 (2006) 691-701
12. Csomós P., Zupkó I., Réthy B., Fodor L., Falkay G., and Bernáth G. Bioorg. Med. Chem. Lett. 16 (2006) 6273-6276
13. Fodor L., Szabó J., Szu{combining double acute accent}cs E., Bernáth G., Sohár P., and Tamás J. Tetrahedron 40 (1984) 4089-4095
14. Fodor L., and MacLean D.B. Can. J. Chem. 65 (1987) 18-26
15. Szabó J., Fodor L., Bani-Akoto E., Talpas G.S., Bernáth G., and Sohár P. Tetrahedron 48 (1992) 4957-4962
16. Fodor L., Bernáth G., Sinkkonen J., and Pihlaja K. J. Heterocycl. Chem. 39 (2002) 927-931
17. Csomós P., Fodor L., Sinkonen J., Pihlaja K., and Bernáth G. Tetrahedron Lett. 47 (2006) 5665-5667
18. Wright Jr. W.B., and Brabander H.J. J. Med. Chem. 11 (1968) 1164-1167
19. Nógrádi T. Monatsh. Chem. 88 (1958) 1087-1094
20. Pletnev A.A., Tian Q., and Larock R.C. J. Org. Chem. 67 (2002) 9276-9287
21. Borza I., Kolok S., Ignácz-Szendrei G., Greiner I., Tárkányi G., Galgóczy K., Horváth C., Farkas S., and Domány G. Bioorg. Med. Chem. Lett. 15 (2005) 5439-5441
22. Spadoni G., Balsamini C., Diamantini G., Tontini A., Giorgio Tarzia G., Marco Mor M., Rivara S., Plazzi P.V., Nonno R., Lucini V., Pannacci M., Franco Fraschini F., and Stankov B.M. J. Med. Chem. 44 (2001) 2900-2912
23. Shibahara F., Kitagawa A., Yamaguchi E., and Murai T. Org. Lett. 8 (2006) 5621-5624
24. Jordan A.D., Luo C., and Reitz A.B. J. Org. Chem. 68 (2003) 8693-8696
25. Takasugi M., Monde K., Katsui M., and Shirata A. Bull. Chem. Soc. Jpn. 61 (1988) 285-289
26. Kutschy P., Suchý M., Monde K., Harada N., Maruškova R., Čurillova Z., Dzurilla M., Miklošova M., Mezencev R., and Mojžiš J. Tetrahedron Lett. 43 (2002) 9489-9492
27. Noland W.E. Organic Synthesis Coll. Vol. 6 (1988), Wiley, New York, NY pp 175-177
28. Sohár P. Nuclear Magnetic Resonance Spectroscopy Vol. 2 (1983), CRC, Boca Raton, FL p 185
29. Thiel W., and Mayer R. J. Prakt. Chem./Chem.-Ztg. 331 (1989) 243-262
30. Fagan G.P., Chapleo C.B., Lane A.C., Myers M., and Roach A.G. J. Med. Chem. 31 (1988) 944-948
31. Acheson R.M., Prince R.J., and Proctor G. J. Chem. Soc. P1 (1979) 595-598
32. Rosemund P., Sauer D., and Trommer W. Chem. Ber. 103 (1970) 496-509