The peculiar reaction of 2-arylazo-1-vinylpyrroles with trifluoroacetic acid: a novel synthesis of 2-methylquinolines

Tetrahedron

Volumn 65, Issue 25, 2009, Pages 4855-4858

  Schmidt, Elena Yu ^a   Senotrusova, Elena Yu ^a   Ushakov, Igor A ^a   Mikhaleva, Al'bina I ^a   Trofimov, Boris A ^a  

^a A E FAVORSKY IRKUTSK INSTITUTE OF CHEMISTRY   (Russian Federation)

Author keywords

2 Arylazo 1 vinylpyrrole; 2 Methylquinoline; Protonation; Trifluoroacetic acid

Indexed keywords

AZO COMPOUND; BENZENE; ELECTROPHILE; NITROGEN; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRROLE DERIVATIVE; QUINALDINE; TRIFLUOROACETIC ACID; VINYL DERIVATIVE;

ADDITION REACTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL BOND; MOLECULAR DYNAMICS; NITROGEN NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PROTON TRANSPORT; SUBSTITUTION REACTION; SYNTHESIS;

EID: 65549097630     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.04.037     Document Type: Article

References (22)

1. Trofimov B.A., Schmidt E.Y., Mikhaleva A.I., Vasil'tsov A.M., Zaitsev A.B., Smolyanina N.S., Senotrusova E.Y., Afonin A.V., Ushakov I.A., Petrushenko K.B., Kazheva O.N., Dyachenko O.A., Smirnov V.V., Schmidt A.F., Markova M.V., and Morozova L.V. Eur. J. Org. Chem. (2006) 4021-4033
2. Rusakov Y.Y., Krivdin L.B., Senotrusova E.Y., Schmidt E.Y., Vasil'tsov A.M., Mikhaleva A.I., Trofimov B.A., Dyachenko O.A., Chekhlov A.N., and Kazheva O.N. Magn. Reson. Chem. (2007) 142-151
3. Schmidt E.Y., Senotrusova E.Y., Ushakov I.A., Protzuk N.I., Mikhaleva A.I., and Trofimov B.A. Russ. J. Org. Chem. 43 (2007) 1495-1501
4. Senotrusova, E. Y. Abstract of the Thesis for Candidate of Chemical Science, Irkutsk, 2007; p 19;
5. Trofimov B.A., Markova M.V., Morozova L.V., Schmidt E.Y., Senotrusova E.Y., Myachina G.F., Myachin Y.A., Vakul'skaya T.I., and Mikhaleva A.I. Polym. Sci. B 49 (2007) 292-296
6. Trofimov B.A., Korostova S.E., Sobenina L.N., Trzhitsinskaya B.V., Mikhaleva A.I., and Sigalov M.V. Zh. Org. Khim. 16 (1980) 1964-1968
7. Trofimov B.A. Advances in Heterocyclic Chemistry Vol. 51 (1990), Academic, San Diego pp 177-301
8. Trofimov B.A. The Synthesis, Reactivity, and Physical Properties of Substituted Pyrroles (1992), Wiley, New York, NY pp 131-298
9. Mikhaleva A.I., Korostova S.E., Vasil'ev A.N., Balabanova L.N., Sokolnikova N.P., and Trofimov B.A. Chem. Heterocycl. Compd. 13 (1977) 1305-1309
10. Kopylova L.I., Korostova S.E., Sobenina L.N., Nesterenko R.N., Sigalov M.V., Mikhaleva A.I., and Trofimov B.A. Zh. Org. Khim. 51 (1981) 1778-1789
11. Morozova L.V., Mikhaleva A.I., Markova M.V., Sobenina L.N., and Trofimov B.A. Russ. Chem. Bull. 45 (1996) 407-409
12. Zhu Z., Wang Y., and Lu Y. Macromolecules 36 (2003) 9585-9593
13. Audebert P., Sadki S., Miomandre F., Hapiot P., and Chane-Ching K. New J. Chem. 27 (2003) 798-804
14. Audebert P., Kamada K., Matsunaga K., and Ohta K. Chem. Phys. Lett. 367 (2003) 62-71
15. Ludwig R. Fresenius' J. Anal. Chem. 367 (2000) 103-128
16. Lazo J.S., Aslan D.C., Southwick E.C., Cooley K.A., Ducruet A.P., Joo B., Vogt A., and Wipf P. J. Med. Chem. 44 (2001) 4042-4049
17. Liou S.S., Zhao Y.L., Chang Y.L., Teng C.M., and Tzeng C.C. Chem. Pharm. Bull. 45 (1997) 1777-1781
18. Behforouz M., Gu Z., Cai W., Horn M.A., and Ahmadian M. J. Org. Chem. 58 (1993) 7089-7091
19. Bringmann G., Reichert Y., and Kane V.V. Tetrahedron 60 (2004) 3539-3574
20. Makhija M.T. Curr. Med. Chem. 13 (2006) 2429-2941
21. Witanovski M., Stefaniak L., and Webb G.A. Annual Reports on NMR Spectroscopy Vol. 11B (1981), Academic, London pp 33-34
22. Taft Jr. R.W. J. Am. Chem. Soc. 74 (1952) 3120-3128