Abstract
Condensation of 2-(cyanomethyl)benzoic acid with 2-aminobenzylamine gave 6,11-dihydro-13H-isoquino[3,2-b]quinazolin-11-one. Its oxidation in nitrobenzene led to the formation of 5,13,5′,13′-hexahydro[6,6′]bi[isoquino[3,2-b]quinazoline]-11,11′-dione, but in dichlorobenzene in the presence of elemental sulfur and iodine it gave the rearrangement product 6H-dibenzo[b,f][1,8]naphthyridin-5-one.
Similar content being viewed by others
References
L. M. Potikha, V. A. Kovtunenko, and A. V. Tarasevich, Khim. Geterotsikl. Soed., 1833 (2007). [Chem. Heterocycl. Comp., 43, 1550 (2007)].
S. Goya, A. Takadate, T. Tanaka, Y. Tsuruda, and H. Ogata, Yakugaku Zasshi, 100, 826 (1980); Chem. Abstr., 94, 65446 (1981).
S. Goya, A. Takadate, T. Tanaka, H. Nagayama, and O. Teisuke, Yakugaku Zasshi, 95, 333 (1975); Chem. Abstr., 83, 43153 (1975).
T. T. Kucherenko, R. Gutsul, V. M. Kisel, and V. A. Kovtunenko, Tetrahedron. 60, 211 (2004).
V. A. Kovtunenko, T. T. Kucherenko, O. V. Shishkin, and V. M. Kisel, Khim. Geterotsikl. Soed., 1408 (2002). [Chem. Heterocycl. Comp., 38, 1242 (2002)].
E. Schefczik, Ger. Pat., 1951516; Chem. Abstr., 75, 37920 (1971).
E. Schefczik, Liebigs Ann Chem., 729, 83 (1969).
L. M. Potikha, V. M. Kisel, N. V. Danileiko, and V. A. Kovtunenko, Khim. Geterotsikl. Soed., 715 (2004). [Chem. Heterocycl. Comp., 40, 603 (2004)].
H. Bekker, W. Berger, G. Domschke, E. Fanghänel, J. Faust, M. Fischer, F. Gentz, K. Gewald, R. Gluch, R. Mayer, K. Müller, D. Pavel, G. Schmidt, K. Schollberg, E. Seiler, and G. Zeppenfeld, Organikum [in Russian], Mir, Moscow, 1992, vol. 1, 245.
W. Borsche, M. Wagner-Roemmich, and J. Barthenheier, Liebigs Ann. Chem., 550, 160 (1942).
M. A. Meyer, Bull. Soc. Chim. Fr., 51, 953 (1932).
R. D. Haworth and G. Sh. Pink, J. Chem. Soc., 2348 (1927).
L. Johnson, J. Org. Chem., 41, 836 (1976).
Author information
Authors and Affiliations
Corresponding author
Additional information
__________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No.2, 273–279, February, 2008.
Rights and permissions
About this article
Cite this article
Potikha, L.M., Gutsul, R.M., Turov, A.V. et al. Condensed isoquinolines 27*. Synthesis and oxidation reactions of 5,13-dihydro-11H-isoquino[3,2-b]quinazolin-11-one. Chem Heterocycl Comp 44, 208–213 (2008). https://doi.org/10.1007/s10593-008-0024-6
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-008-0024-6