A convenient method has been developed for the synthesis of 2,4-dihydro-6H-thieno[3,4-c]pyrazol-6-ones by means of an intramolecular cyclization of 4-sulfanylmethylpyrazole-3-carboxylic acids. The latter were prepared from ethyl 4-formylpyrazole-3-carboxylates via the intermediate 4-hydroxy-methyl-, 4-chloromethyl-, and 4-thioureidomethyl derivatives.
Similar content being viewed by others
References
M. K. Bratenko, M. M. Barus, and M. V. Vovk, Khim. Geterotsikl. Soedin., 243 (2010). [Chem. Heterocycl. Compd., 46, 196 (2010)].
G. Menozzi, L. Mosti, P. Schenone, M. D'Amico, A. Filippelli, and F. Rossi, Farmaco, 47, 1495 (1992).
M. Matsuo, K. Tsuji, N. Konishi, and K. Nakamura, EU Pat. Appl. 418845; Chem. Abstr., 115, 71593z (1991).
Z. Li, G. D. Francisco, W. Hu, P. Labthavikul, P. J. Petersen, A. Severin, G. Singh, Y. Yang, B. A. Rasmussen, Y.-I. Lin, J. S. Skotnicki, and T. S. Mansour, Bioorg. Med. Chem. Lett., 13, 2591 (2003).
V. J. Bauer, R. P. Williams, and S. R. Safir, J. Med. Chem., 14, 454 (1971).
T. S. Chou and R. C. Chang, J. Org. Chem., 58, 493 (1993).
T.-S. Chou and R.-C. Chang, Heterocycles, 36, 2839 (1993).
P. G. Baraldi, H. El-Kashef, S. Manfredini, M. J. Pineda de las Infantas, R. Romagnoli, and G. Spalluto, Synthesis, 1331 (1998).
K. T. Potts and D. McKeough, J. Am. Chem. Soc., 96, 4276 (1974).
S. Kagabu and I. Kaku, Biosci. Biotechnol. Biochem., 57, 1899 (1993).
M. K. Bratenko, M. M. Barus, and M. V. Vovk, Khim. Geterotsikl. Soedin., 1817 (2009). [Chem. Heterocycl. Compd., 45, 1464 (2009)].
Author information
Authors and Affiliations
Corresponding author
Additional information
*For Communication 6, see [1].
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1657-1661, October, 2012.
Rights and permissions
About this article
Cite this article
Bratenko, M.K., Barus, M.M. & Vovk, M.V. Polyfunctional pyrazoles. 7*. Ethyl 1-aryl-4-formylpyrazole-3-carboxylates in the synthesis of 2-aryl-2,4-dihydro-6H-thieno-[3,4-c]pyrazol-6-ones. Chem Heterocycl Comp 48, 1545–1549 (2013). https://doi.org/10.1007/s10593-013-1171-y
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-013-1171-y