Abstract
This study offers an access to 21 new heterocyclic compounds representing pyrrole derivatives of 4-amino-4H-1,2,4-triazole-3-thiols or 1,3,4-oxadiazole-2-thiols. The principal synthetic approach is based on the cyclization of substituted potassium 2-(pyrrolecarbonyl)hydrazine-1-carbodithionate with hydrazine hydrate to 5-(substituted pyrrolyl)-4-amino-4H-1,2,4-triazole-3-thiols, followed by S-alkylation with methyl iodide or benzyl chloride. Among the resulted thirteen S-alkyl derivatives, five 1,3,4-oxadiazole derivatives have been isolated as secondary products and their formation is explained as being the result of S-alkylation of intermediate 1,3,4-oxa-diazole-2-thiols, generated in the alkaline medium.
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M. C. Sarvà, G. Romeo, F. Guerrera, M. Siracusa, L. Salerno, F. Russo, A. Cagnotto, and M. Goegan, T. Mennini, Bioorg. Med. Chem., 10, 313 (2002).
A. Kakefuda, T. Suzuki, T. Tobe, A. Tahara, S. Sakamoto, and S. Tsukamoto, Bioorg. Med. Chem., 10, 1905 (2002).
S. N. Pandeya, D. Sriram, G. Nath, and E. de Clerc, Arzneimittelforsch., 50, 55 (2000).
B. S. Holla, K. N. Poojary, B. Kalluraya, and P. V. Gowda, Farmaco, 51, 793 (1996).
L. Labanauskas, V. Kalcas, E. Udrenaite, P. Gaidelis, A. Brukstus, and V. Dauksas, Pharmazie, 56, 617 (2001).
N. G. Ulusoy, N. Ergenc, G. Otuk, and M. Kiraz, Boll. Chim. Farm., 146, 417 (2001).
T. kbarzadeh, S. A. Tabatabai, M. J. Khoshnoud, B. Shafaghi, and A. Shafiee, Bioorg. Med. Chem., 11, 769 (2003).
K. Khanna, R. M. Weier, Y. Yu, P. Collins, J. Miyashiro, C. Koboldt, A. Veenhuizen, J. Currie, K. Seibert, and P. Isakson, J. Med. Chem., 40, 1619 (1997).
G. Danhardt, W. Kiefer, G. Kramer, S. Maehrlein, U. Nove, and B. Flebich, Eur. J. Med. Chem., 35, 499 (2000).
N. Amishiro, A. Okamoto, C. Murakata, T. Tamaoki, M. Okabe, and J. Saito, J. Med. Chem., 42, 2946 (1999).
R. Perez-Tomas, B. Montaner, E. Llagostera, and V. Soto-Cerrato, Biochem. Pharmacol., 66, 1447 (2003).
M. A. Evans, D. C. Smith, J. M. Holub, A. Argenti, M. Hoff, G. A. Dalglish, D. L. Wilson, B. M. Taylor, J. D. Berkowitz, B. S. Burnham, K. Krumpe, J. T. Gupton, T. C. Scarlett, R. Durham, and I. H. Hall, Arch. Pharm., 336, 181 (2003).
G. A. Pinna, G. Loriga, G. Murineddu, G. Grella, M. Mura, L. Vargiu, C. Murgioni, and P. La Colla, Chem. Pharm. Bull., 49, No 111406 (2001).
W. Malinka, M. Sieklucka-Dziuba, G. Rajtar, R. Rejdak, K. Rejdak, and Z. Kleinrok, Pharmazie, 55, 9 (2000).
A. Bijev and P. Prodanova, J. Univ. Chem. Technol. Met. (Sofia), 39, 141 (2004).
V. P. Himatkumar, P. S. Fernandes, and K. A. Vyas, Indian J. Chem., 29B, 135 (1990).
R. W. Young and K. H. Wood, J. Am. Chem. Soc., 77, 400 (1955).
J. Sandstrom, Adv. Heterocycl. Chem., 9, 165 (1968).
S. N. Sawhney, R. K. Tomer, O. Parkash, I. Prakash, and S. P. Singh, Indian J. Chem., 19B, 415 (1980).
E. Hoggarth, J. Chem. Soc., 4811 (1952).
G. S. Gadaginamath, R. G. Joshi, and A. G. Kamat, Rev. Roum. Chim., 40, 475 (1995).
J. R. Reid and N. D. Heindel, J. Heterocycl. Chem., 13, 925 (1976).
V. Jakubkiene, M. M. Burbuliene, G. Mekuskiene, E. Udrenaite, P. Gaidelis, and P. Vainilavicius, Farmaco, 58, 323 (2003).
G. Sahin, E. Palaska, P. Kelicen, R. Demirdamar, and G. Altinok, Arzneimittelforsch., 51, 478 (2001).
G. Sahin, E. Palaska, M. Ekizoglu, and M. Ozalp, Farmaco, 57, 539 (2002).
S. A. Rostom, M. A. Shalaby, and M. A. El-Demellawy, Eur. J. Med. Chem., 38, 959 (2003).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 383–391, March, 2007.
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Bijev, A.T., Prodanova, P. Derivatives of 4-amino-4H-1,2,4-triazole-3-thiols linked to the pyrrole cycle and some products of their S-alkylation. Chem Heterocycl Compd 43, 306–313 (2007). https://doi.org/10.1007/s10593-007-0046-5
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DOI: https://doi.org/10.1007/s10593-007-0046-5