Design, Synthesis and Characterization of Pyrimidine based Thiazolidinedione Derivatives
Novel thiazolidine-2,4-dione (TZD) based pyrimidine derivatives have been synthesized by Knoevenagel Condensation reaction between TZD and amino pyrimidinyl aliphatic aldehydes followed by heterogeneous metal reduction. Synthetic strategy involved nucleophillic substitution of hydroxyl protected six membered aliphatic chain on 4,6-dichloropyrimidine followed by Suzuki coupling. This approach is regio-selective, efficient and versatile for synthesis of such analogs.
General Scheme for Synthesis of Compounds:
 S. P. Singh, S. S. Parmar, K. Raman and Stenberg, Chem. Rev. 81, 175 (1981).
 M.T. Omar, M. A. Kasem, J. Heterocyclic Chem., 18, 1413 (1981).
 B. C. Sekhar, J. Heterocyclic Chem., 41, 807 (2004).
 H. Yanagisawa, M. Takamura, E. Yamada, S. Fujita, T. Fujiwara, M. Yachi, A. Isobe, Y. Hagisawa, Bioorg. Med. Chem. Lett., 10 (4), 373 (2000).
 D. A. Heerding, L. T. Christmann, T. J. Clark, D. J. Holmes, S. F. Rittenhouse, D. T. Takata, J. W. Venslavsky, Bioorg. Med. Chem. Lett. 13 (21), 377 (2003).
 B. C. Cantello, M. A. Cawthorne, D. Haigh, R. M. Hindley, S. A. Smith, P. L. Thurlby, Bioorg. Med. Chem. Lett., 4 (10), 1181 (1994).
 S. Allen, B. N. Newhouse, A. S. Anderson et.al, Bioorganic and Medicinal Chemistry Letters, 14 (7), 1619 (2004).
Keywords - Thiazolidine-2,4-dione(TZD), Suzuki Coupling, Knoevenagel Condensation.