Synthesis of novel and hardly-obtainable 1,2,3-triazoles with potential antitumoral activity by a diazo-transfer reaction from 5,7-dinitro-3-diazo-1,3-dihydro-2H-indol-2-one to enaminones

Heterocyclic Communications

Volumn 9, Issue 3, 2003, Pages 235-238

  Ferreira Melo, Júlio Onésio ^a   Donnici, Claudio Luis ^a   Augusti, Rodinei ^a   Paz Lopes, Míriam Teresa ^a   Mikhailovskii, Alexander Grigorievitch ^b  

^a FEDERAL UNIVERSITY OF MINAS GERAIS   (Brazil)

^b INSTITUTE OF TECHNICAL CHEMISTRY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

5,7 DINITRO 3 DIAZO 1,3 DIHYDRO 2H INDOL 2 ONE; ANTINEOPLASTIC AGENT; KETONE DERIVATIVE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 0141922915     PISSN: 07930283     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (21)

1. T. I. Godovikova, E. L. Ignat'eva and L. I. Khmel'nitskii, Chem Heterocycl. Compd. 25, 113 (1989);
2. (b) R.R. Talekar and R. H. Wightman, Tetrahedron 53, 3831 (1997);
3. (c) L. Bertelli, G. Biagi, I. Giorgi, C. Manera, O. Livi, V. Scartoni, L. Betti, G. Giannaccini, L. Trincavelli and P.L. Barili, Eur. J. Med. Chem. 33, 113 (1998);
4. (d) J.M. Contelles and M.R. Fernández, Tetrahedron Lett 41, 381 (2000);
5. (e) E.W. Gordon, M.A. Gallop, R.W. Barrett, W.J. Dower and S.P.A. Fodor, J. Med. Chem. 37, 1233 (1994);
6. (f) N.K. Terret, M. Gardner, D.W. Gordon, R.J. Kobylecki and J. Steele, Tetrahedron 51, 8135 (1995).
7. I.P. Nnane, V.C.O. Njar and A.A. Brodie, J. Steroid. Biochem. 78, 241 (2001).
8. D.R. Buckle and C.J.M. Rockell, J. Chem. Soc. Perkin Trans I 627 (1982).
9. S.T. Abu-Orabi, M.A. Atfah, I. Jibril, F.M. Mari'i and A. Al-Sheikh Ali, J. Heterocyclic Chem. 26, 1461 (1989).
10. Degl'Innocenti, P. Scafato, A. Capperucci, L. Bartoletti, A. Mordini and G. Reginato, Tetrahedron Lett. 36, 9031 (1995).
11. B.E. Blass, A.L.F. Coburn, C.L. Hunn, M.S.P. Natchus, J.S.T. Portlock and R. Wood, Tetrahedron Lett. 43, 4059 (2002).
12. A.R. Katritzky, M. Qi, D. Feng, G. Zhang, M.C. Griffith and K. Watson, Org. Lett. 1(8), 1189 (1999).
13. R. Augusti and C. Kascheres, Tetrahedron 50, 6723 (1994).
14. R. Augusti and C. Kascheres, J. Org. Chem. 58, 7079 (1993).
15. J.V. Greenhill, Chem. Soc. Rev. 6, 277 (1977).
16. G.A. Romeiro, L.O.R. Pereira, M.C.B.V. Souza, V.F. Ferreira and A.C. Cunha, Tetrahedron Lett. 38, 5103 (1997).
17. C. Grundmann and H. Haldenwanger, Angew. Chem. 62, 410 (1950).
18. V.S. Shklyaev, B.B. Aleksandrov, A.G. Mikhailovskii and M.I. Vakhrin, Khim. Geterotsikl 9, 1239 (1989);
19. (b) V.S. Shklyaev, B.B. Aleksandrov, M.S. Gavrilov, A.G. Mikhailovskii and M.I. Vakhrin, Khim. Geterotsikl 7, 939 (1988).
20. 2: 267.19485).
21. 2 atmosphere at room temperature, it was added a solution of enaminones (5, 8) or enamines 6 (3.70 mmol in 8 mL of anhydrous acetonitrile). After 0.5 h, it was slowly added a solution of mesyl azide 4 (5.0 mmol in 1 mL of anhydrous acetonitrile): stirring was kept for 48 h and the reaction was quenched with NaOH (10% w/w). The organic layer separated was dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure to give a residue which was extracted with methylene chloride (3 x 30 mL), and which was subsequently removed under reduced pressure.