Abstract
Esters of 4-R-4,5-dihydro-1H-pyrazole-3,5,5-tricarboxylic acids with chlorine yield esters of 4-R-5-chloro-4,5-dihydro-3H-pyrazole-3,3,5-tricarboxylic acids that at thermolysis provide the esters of the corresponding 2-chlorocyclopropanetricarboxylic acid. The same esters react with bromine in dichloromethane at room temperature to give a mixture of esters of the corresponding 1H-pyrazole-3,5-dicarboxylic acids and 5-bromo-4,5-dihydro-3,3,5-tricarboxylic acids. From 5,5-diethyl 3-methyl 4,5-dihydro-1Hpyrazole-3,5,5-tricarboxylate and N-iodosuccinimide or a system iodine-silver trifluoroacetate we obtained 1,1-diethyl 2-methyl 2-iodocyclopropane-1,1,2-tricarboxylate.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
REFERENCES
Molchanov, A.P., Stepakov, A.V., Kostikov, R.R., and Baird, M.S., Synlett, 2000, no. 2, pp. 219-220.
Molchanov, A.P., Stepakov, A.V., and Kostikov, R.R., Zh. Org. Khim., 2001, vol. 37, no. 1, pp. 137-143.
Molchanov, A.P., Stepakov, A.V., and Kostikov, R.R., Zh. Org. Khim., 2002, vol. 38, no. 2, pp. 286-289.
Alonso, M.E., Pekerar, S.V., and Borgo, M.L., Magnetic. Res. Chem., 1990, vol. 28, no. 11, pp. 956-962.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Molchanov, A.P., Stepakov, A.V., Boitsov, V.M. et al. Reaction of 4,5-Dihydro-1H-pyrazole-3,5,5-tricarboxylic Acids Esters with Halogens. Russian Journal of Organic Chemistry 38, 1666–1670 (2002). https://doi.org/10.1023/A:1022574404328
Issue Date:
DOI: https://doi.org/10.1023/A:1022574404328