An expeditious one-pot synthesis has been developed to obtain aryl(hetaryl)-substituted thiazolylphthalazine-1,4-diones via a multicomponent approach. The reaction of phenacyl bromides with thiosemicarbazide and phthalic anhydride afforded arylthiazolylphthalazine-1,4-diones. The reaction of 3-(2-bromoacetyl)coumarins with thiosemicarbazide and phthalic anhydride afforded hetaryl-containing 2-thiazolylphthalazine-1,4-diones under the same reaction conditions in excellent yields. The structures of all the synthesized compounds were confirmed by their analytical and spectral data.
Similar content being viewed by others
References
R. W. Armstrong, A. P. Combs, P. A. Tempest, S. D. Brown, and T. A. Keating, Acc. Chem. Res., 29, 123 (1996).
Dömling and I. Ugi, Angew. Chem., Int. Ed., 39, 3168 (2000).
Strecker, Justus Liebigs Ann. Chem., 75, 27 (1850).
R. Robinson, J. Chem. Soc., 111, 876 (1917).
Hantzsch, Justus Liebigs Ann. Chem., 215, 1 (1882).
R. Bossio, C. F. Marcos, S. Marcaccini, and R. Pepino, Tetrahedron Lett., 38, 2519 (1997).
G. F. Ross, E. Herdtweck, and I. Ugi, Tetrahedron, 58, 6127 (2002).
K. D. Hargrave, F. K. Hess, and J. T. Oliver, J. Med. Chem., 26, 1158 (1983).
W. C. Patt, H. W. Hamilton, M. D.Taylor, M. J. Ryan, D. G. Taylor, Jr., C. J. C. Connolly, A. M. Doherty, S. R. Klutchko, I. Sircar, B. A. Steinbaugh, B. L. Batley, C. A. Painchaud, S. T. Rapundalo, B. M. Michniewicz, and S. C. J. Olson, J. Med. Chem., 35, 2562 (1992).
F. W. Bell, A. S. Cantrell, M. Högberg, S. R. Jaskunas, N. G. Johansson, C. L. Jordon, M. D. Kinnick, P. Lind, J. M. Morin, Jr., R. Noréen, B. Öberg, J. A. Palkowitz, C. A. Parrish, P. Pranc, C. Sahlberg, R. J. Ternansky, R. T. Vasileff, L. Vrang, S. J. West, H. Zhang, and X.-X. Zhou, J. Med. Chem., 38, 4929 (1995).
J. Druey and B. H. Ringier, Helv. Chim. Acta, 34, 195 (1951).
K.-D. Gundermann, H. Fiege, and G. Klockenbring, Justus Liebigs Ann. Chem., 738, 140 (1970).
F. Gómez Contreras, M. Lora-Tamayo, and A. M. Sanz, Heterocycles, 28, 791 (1989).
V. R. Rao and V. R. Reddy, Khim. Geterotsikl. Soedin., 465 (2008). [Chem. Heterocycl. Compd., 44, 360 (2008)].
V. S. R. Chunduru and V. R. Rao, J. Sulfur Chem., 31, 545 (2010).
V. S. R. Chunduru and V. Rajeswar Rao, J. Chem. Res., 34, 50 (2010).
M. C. Cardia, S. Distinto, E. Maccioni, A. Plumitallo, L. Sanna, M. L. Sanna, and S. Vigo, J. Heterocycl. Chem., 46, 674 (2009).
V. R. Rao and T. V. P. Rao, Indian J. Chem., 25B, 413 (1986).
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 628–632, April, 2013.
Rights and permissions
About this article
Cite this article
Chunduru, V.S.R., Vedula, R.R. One-pot synthesis of aryl(hetaryl)-thiazolylphthalazine-1,4-diones via a multicomponent approach. Chem Heterocycl Comp 49, 586–590 (2013). https://doi.org/10.1007/s10593-013-1285-2
Received:
Revised:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-013-1285-2