Abstract
Reaction of 2-amino-4,5,6,7-tetrahydro-1-benzoselenophene-3-carbonitrile with ethylenediamine in the presence of a catalytic amount of carbon disulfide afforded 2-amino-3-(4,5-dihydro-1H-imidazol-2-yl)-4,5,6,7-tetrahydro-1-benzoselenophene. Cyclocondensation of the latter with triethyl orthoformate, benzaldehyde, and carbon disulfide gave tetracyclic imidazobenzoselenophenopyrimidine derivatives. Treatment of 2,3,5,6,8,9,10,11-octahydroimidazo[2,1-c][1]benzoselenopheno[3,2-e]pyrimidine-5-thione with hydrazine hydrate led to the corresponding 5-hydrazino derivative whose reactions with triethyl orthoformate and sodium nitrite were accompanied by closure of 1,2,4-triazole and tetrazole rings, respectively. Fused benzoseleno-phenopyrimidine systems were also obtained by reaction of 2-amino-4,5,6,7-tetrahydrobenzo-1-selenophene-3-carbonitrile with formamide, carbon disulfide, and phenyl isothiocyanate. Some newly synthesized compounds were tested for antimicrobial and antifungal activity.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
REFERENCES
Litvinov, V.P. and Dyachenko, V.D., Russ. Chem. Rev., 1997, vol. 66, p. 923.
Paulmier, C., Selenium Reagents and Intermediates in Organic Synthesis, Oxford: Pergamon, 1986.
Wirth, T., Tetrahedron, 1999, vol. 55, p. 1; Organoselenium Chemistry. Topics in Current Chemistry, Wirth, T., Ed., Berlin: Springer, 2000, p. 208.
Organoselenium Chemistry, A Practical Approach, Black, T.G., Ed., Oxford: Oxford Univ., 1999.
Atanassov, P.K., Zhou, Y., Linden, A., and Heimgartner, H., Helv. Chim. Acta, 2002, vol. 85, p. 1102.
Gasparian, A.V., Yao, Y.J., Lu, J., Yemelyanov, A.Y., Lyakh, L.A., Slaga, J.T., and Budunova, I.V., Mol. Cancer Ther., 2002, vol. 1, p. 1079.
Fleming, J., Ghose, A., and Harrison, P.R., Nutr. Cancer, 2001, vol. 40, p. 42.
Ghose, A., Fleming, J., El-Bayoumy, K., and Harrison, P.R., Cancer Res., 2001, vol. 61, p. 7479.
Wu, W., Murakami, K., Koketsu, M., and Saiki, I., Anticancer Res., 1999, vol. 19, p. 5375.
Hu, C., Zhang, P., Li, H., Ji, Z., and Liu, B., Huaxue Tongbao, 2002, vol. 65, p. 162; Chem. Abstr., 2002, vol. 137, no. 169 434.
Koketsu, M., Senda, T., and Ishihara, H., JPN Patent no. 2000-119 263, 2000; Chem. Abstr., 2000, vol. 132, no. 293 768.
Janzuu, S., Appell, G., Chaudiere, J., and Yadan, J.-C., JPN Patent no. 11-140 067, 1999; Chem. Abstr., 1999, vol. 131, no. 32 054.
Koketsu, M., Tanaka, K., Takenaka, Y., Kwong, C.D., and Ishihara, H., Eur. J. Pharm. Sci., 2002, vol. 15, p. 307.
Sibor, J. and Pazdera, P., Molecules, 1996, vol. 1, p. 157.
Abdel-Hafez, Sh.H., Phosphorus, Sulfur, Silicon, 2003, vol. 178, p. 2563.
Abbady, M.A. and Abdel-Hafez, Sh.H., Phosphorus, Sulfur, Silicon, 2000, vol. 160, p. 121.
Abbady, M.A., Abdel-Hafez, Sh.H., Kandeel, M.M., and Abdel-Monem, M.I., Molecules, 2003, vol. 8, p. 622.
Radwan, Sh.M. and El-Kashef, H.S., Farmaco, 1998, vol. 53, p. 113.
Youssefyeh, R.D., Brown, R.E., Wilson, J., Shahm, U., et al., J. Med. Chem., 1984, vol. 27, p. 1639.
Carrod, L.P. and Grady, F.D., Antibiotics and Chemotherapy, Edinburgh: Churchill Livingston, 1972, 3rd ed., p. 477.
Cremer, A., Antibiotic Sensitivity and Assay Tests, London: Butterworth, 1980, 4th ed., p. 521.
Author information
Authors and Affiliations
Additional information
__________
From Zhurnal Organicheskoi Khimii, Vol. 41, No. 3, 2005, pp. 406–410.
Original English Text Copyright © 2005 by Abdel-Hafez.
The original article was submitted in English.
Rights and permissions
About this article
Cite this article
Abdel-Hafez, S.H. Selenium-Containing Heterocycles. Synthesis and Reactions of 2-Amino-4,5,6,7-tetrahydro-1-benzoselenophene-3-carbonitrile with Anticipated Biological Activity. Russ J Org Chem 41, 396–401 (2005). https://doi.org/10.1007/s11178-005-0177-z
Received:
Issue Date:
DOI: https://doi.org/10.1007/s11178-005-0177-z