Abstract
A series of 3-[-4-phenyl-thiazol-2-yl)-hydrazono]-1,3-dihydro-indole-2-one(4a–4g) and 3-{[4-(2-oxo-2H-chromen-3-yl)-thiazol-2-yl]-hydrazono}-1,3-dihydro-indol-2-one(6a–6d) has been prepared in a one-step procedure from condensation reaction of isatin(1), thiosemicarbazide(2) and bromoacetophenones(3)/or 3-(2-bromoacetyl)coumarins(4). The method provides a simple and efficient route to prepare the compounds in good yields and in a short experimental time as compared to its stepwise procedure.
Similar content being viewed by others
References
Liéby-Muller F., Constantieux T., Rodriguez J., Synlett., 2007, (8), 1323
Zhu J., Bienaymé H., Eds., Multi-component Reactions, Wiley-VCH: Weinheim, 2005, 76
Nicolaou K. C., Edmonds D. J., Bulger P. G., Angew. Chem. Int. Ed., 2006, 45(43), 7134
Barber D. M., Sanganee H., Dixon D. J., Chem. Commun., 2011, 47(15), 4379
Tietze L. F., Brasche G., Gericke K. M., Domino Reactions in Organic Synthesis, Wiley-VCH, Weinheim, 2006, 542
Padwa A., Bur S. K., Tetrahedron, 2007, 63(25), 5341
Brauch S., van Berkela S. S., Westermann B., Chem. Soc. Rev., 2013, 42(12), 4948
Wang H. J., Mo L. P., Zhang Z. H., J. Comb. Chem., 2011, 13(2), 181
Yao C., Lei S., Wang C., Li T., Yu C., Wang X., Tu S., J. Heterocycl. Chem., 2010, 47(1), 26
Medvedev A., Igosheva N., Crumeyrolle-A. M., Glover V., Stress, 2005, 8(3), 175
Medvedev A., Buneeva O., Glover V., Biologics, 2007, 1(2), 151
Pandeya S. N., Smitha, S., Jyoti M., Sridhar S. K., Acta Pharm., 2005, 55(1), 27
Pandeya S. N., Yogeeswari P., Sriram D., De Clercq E., Pannecouque C., Witvrouw M., Chemotherapy, 1999, 45(3), 192
Tarek A. F., Bin-Jubair F. A. S., Int. J. Res. Pharm. Sci., 2010, 1(2), 113
Chiyanzu I., Clarkson C., Smith P. J., Lehman J., Rosenthal P. J., Chibale K., Bioorg. Med. Chem., 2005, 13(9), 3249
Verma M., Pandeya S. N., Singh K. N., Stables J. P., Acta Pharm., 2004, 54(1), 49
Pandeya S. N., Sriram D., Nath G., De Clercq E., Farmaco., 1999, 54(9), 624
Holla B. S., Rao B. S., Shridhara K., Akbaerali P. M., Farmaco., 2000, 55(5), 388
Bhamaria R. P., Bellare R. A., Deliwala C. V., Indian J. Exp. Biol., 1968, 6(1), 62
Pandey S. N., Smitha S., Stables J. P., Arch. Pharm. Pharm. Med. Chem., 2002, 335(4), 129
Cerchiaro G., da Costa Ferreira A. M., J. Braz. Chem. Soc., 2006, 17(8), 1473
Da Silva J. F. M., Garden S. J., Pinto A. C., J Braz. Chem. Soc., 2001, 12(3), 273
Yamaguchi Y., Clin. Chem., 1978, 24(12), 2178
Broadhurst A. V., Roberts N. A., Ritchie A. J., Handa B. K., Kay C., Anal. Biochem., 1991, 193(2), 280
Bonte W., Johansson J., Garbe G., Berg S., Arch. Kriminol., 1976, 158(5/6), 163
Quiroga J., Hernandez P., Insuasty B., Abonia R., Cobo J., Sanchez A., Nogueras M., Low J. N., J. Chem. Soc. Perkin Trans. 1, 2002, 4, 555
Hutchinson I., Jennings S. A., Vishnuvajjala B. R., Westwell A. D., Stevens M. F. G., J. Med. Chem., 2002, 45(3), 744
Kalkhambkar R. G., Kulkarni G. M., Shivkumar H., Rao R. N., Eur. J. Med. Chem., 2007, 42(10), 1272
Kulkarni M. V., Kulkarni G. M., Lin C. H., Sun C. M., Curr. Med. Chem., 2006, 13(23), 2795
Rajeswar R. V., Padmanabha R. T. V., Indian J. Chem., 1986, 25B(4), 413
Kondratieva M. L., Pepeleva A. V., Belskaia N. P., Koksharov A. V., Groundwater P. V., Robeyns K., Meervelt L. V., Dehaen W., Fan Z. J., Bakulev V. A., Tetrahedron, 2007, 63(14), 3042
Daka K. S., Chaudhary H. S., Sharma K. S., Pujari H. K., Indian J. Chem., 1976, 14B(5), 541
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Aychiluhim, T.B., Vedula, R.R. One pot, multi-component synthesis of 3-[4-aryl-thiazol-2-yl)-hydrazono]-1,3-dihydro-indole-2-one. Chem. Res. Chin. Univ. 30, 601–604 (2014). https://doi.org/10.1007/s40242-014-4036-8
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s40242-014-4036-8