Abstract
The aminothiadiazole (II) on treatment with aromatic aldehydes yielded Schiff bases, which cyclized to thiazolidinone derivatives by reaction with thioglycolic acid. Reaction of II with phenyl isocyanate and phenyl isothiocyanate afforded the carbamide and carbothiamide derivatives, respectively, which on reaction with malonic acid in acetyl chloride gave barbituric and thiobarbituric acid derivatives. However, reaction of carbon disulfide and methyl iodide with II gave dithiocarbamidate derivative which on treatment with ethylenediamine or o-phenylenediamine gave the condensed N-imidazolylthiadiazolylamine derivatives.
[1] Kumar, S., J. Org. Chem. 67, 8842 (2002). http://dx.doi.org/10.1021/jo020493l10.1021/jo020493lSearch in Google Scholar PubMed
[2] Ram, V. J., Pandey, H. K., and Vlietinck, A. T., J. Heterocycl. Chem. 18, 1277 (1981). Search in Google Scholar
[3] Chakrabarti, J. K., Horman, L., Hotten, T. M., Pullar, I. A., Tupper, D. E., and Wright, F. C., J. Med. Chem. 23, 878 (1980). http://dx.doi.org/10.1021/jm00182a01310.1021/jm00182a013Search in Google Scholar PubMed
[4] Sudabeh, P. J. and Raymond, C., J. Heterocycl. Chem. 23, 1571 (1986). http://dx.doi.org/10.1002/jhet.557023056310.1002/jhet.5570230563Search in Google Scholar
[5] Singh, H. and Yadav, L. S., Agric. Biol. Chem. 40, 759 (1976). Search in Google Scholar
[6] Chaaban, I. and Oji, O. O., J. Indian Chem. Soc. 61, 523 (1984). Search in Google Scholar
[7] Aly, A. A., Phosphorus, Sulfur Silicon Relat. Elem. 178, 2415 (2003). http://dx.doi.org/10.1080/1042650039022109610.1080/10426500390221096Search in Google Scholar
[8] Aly, A. A., Chin. J. Chem. 21, 339 (2003). http://dx.doi.org/10.1002/cjoc.2003021032410.1002/cjoc.20030210324Search in Google Scholar
[9] Amine, M. S., Eissa, A. M. F., Shaaban, A. F., El-Sawy, A. A., and El-Sayed, R., Indian J. Chem. 37B, 1153 (1998). Search in Google Scholar
[10] Amine, M. S., Eissa, A. M. F., Shaaban, A. F., El-Sawy, A. A., and El-Sayed, R., Indian J. Chem. 129, 19 (1998). Search in Google Scholar
[11] Feiberg, I., Fien, G., and Walker, J. M., Science 198, 847 (1977). http://dx.doi.org/10.1126/science.2145310.1126/science.21453Search in Google Scholar PubMed
[12] Lien, E. J. and Hussain, M., J. Med. Chem. 14, 138 (1971). http://dx.doi.org/10.1021/jm00284a01410.1021/jm00284a014Search in Google Scholar PubMed
[13] Wright, W. B. and Brabander, H. J., J. Org. Chem. Soc. 19, 711 (1971). Search in Google Scholar
[14] Kokila, D. and Boxi, A. J., J. Indian Chem. Soc. 69, 212 (1992). Search in Google Scholar
[15] Leifert, C., Chidbouree, S., Hampson, S., Workman, S., Sigee, D., Epton, H. A., and Harbour, A., J. Appl. Bacteriol. 78, 97 (1995). Search in Google Scholar
© 2006 Institute of Chemistry, Slovak Academy of Sciences
