Abstract
Cyclization of 2-(2-{4-[allylamino(thioxo)methyl]piperazin-1-yl}ethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione by the action of iodine, bromine, or sulfuryl chloride gave 2-(2-{4-[4,5-dihydro-5-(halomethyl)-thiazol-2-yl]piperazin-1-yl}ethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione hydrohalides which were converted into 2-{2-[4-(5-methylthiazol-2-yl)piperazin-1-yl]ethyl}-1H-benzo[de]isoquinoline-1,3(2H)-dione.
Similar content being viewed by others
References
Zborovskii, Yu.L., Orysyk, V.V., Staninets, V.I., Rusanov, E.B., and Chernega, A.N., Russ. J. Org. Chem., 2007, vol. 43, p. 1030.
Gakhar, H.K., Bhardwaj, S., and Baveja, P., Indian J. Chem., Sect. B, 1977, vol. 15, p. 347; Creeke, P.I. and Mellor, J.M., Tetrahedron Lett., 1989, vol. 30, p. 4435; Tkachenko, S.E., Pushin, A.N., Sokolov, V.B., Fedoseev, V.M., and Martynov, I.V., Khim. Geterotsikl. Soedin., 1998, p. 381.
Braňa, M.F., Cacho, M., Garcsia, M.A., de Pascual-Teresa, B., Ramos, A., Dominguez, M.T., Pozuelo, J.M., Abradelo, C., Rey-Stolle, M.F., Yuste, M., Báňez-Coronel, M.and Lacal, J.C., J. Med. Chem., 2004, vol. 47, p. 1391; Antonini, I., Volpini, R., Dal Ben, D., Lambertucci, C., and Cristalli, G., Bioorg. Med. Chem., 2008, vol. 16, p. 8440; Zhu, H., Huang, M., Yang, F., Chen, Y., Miao, Z.-H., Qian, X.-H., Xu, Y.-F., Qin, Y.-X., Luo, H.-B., Shen, X., Geng, M.-Y., Cai, Y-J., and Ding, J., Mol. Cancer Ther., 2007, vol. 6, p. 484; http://mct.aacrjournals.org/content/6/2/484.full.pdf+html.
Gdanets, M., Simonov, Yu.A., Chumakov, Yu.M., Soboleva, S.G., Varava, V.M., Sava, V.M., and Andronati, S.A., Russ. J. Gen. Chem., 1997, vol. 67, p. 141; Simonov, Yu.A., Chumakov, Yu.M., Soboleva, S.G., Varava, V.M., and Andronati, S.A., Dokl. Akad. Nauk Ukrainy, 1994, no. 2, p. 150.
Bruker 2003. SADABS, SAINT, SHELXTL, SMART, Madison, WI, USA: Bruker AXS.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © Yu.L. Zborovskii, V.V. Orysyk, V.I. Staninets, V.V. Bon’, 2011, published in Zhurnal Organicheskoi Khimii, 2011, Vol. 47, No. 6, pp. 865–869.
Rights and permissions
About this article
Cite this article
Zborovskii, Y.L., Orysyk, V.V., Staninets, V.I. et al. Halocyclization of 2-(2-{4-[allylamino(thioxo)methyl]piperazin-1-yl}ethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione. Russ J Org Chem 47, 881–885 (2011). https://doi.org/10.1134/S107042801106008X
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S107042801106008X