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One pot, multi-component synthesis of 3-[4-aryl-thiazol-2-yl)-hydrazono]-1,3-dihydro-indole-2-one

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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.

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References

  1. Liéby-Muller F., Constantieux T., Rodriguez J., Synlett., 2007, (8), 1323

    Google Scholar 

  2. Zhu J., Bienaymé H., Eds., Multi-component Reactions, Wiley-VCH: Weinheim, 2005, 76

    Book  Google Scholar 

  3. Nicolaou K. C., Edmonds D. J., Bulger P. G., Angew. Chem. Int. Ed., 2006, 45(43), 7134

    Article  CAS  Google Scholar 

  4. Barber D. M., Sanganee H., Dixon D. J., Chem. Commun., 2011, 47(15), 4379

    Article  CAS  Google Scholar 

  5. Tietze L. F., Brasche G., Gericke K. M., Domino Reactions in Organic Synthesis, Wiley-VCH, Weinheim, 2006, 542

    Book  Google Scholar 

  6. Padwa A., Bur S. K., Tetrahedron, 2007, 63(25), 5341

    Article  CAS  Google Scholar 

  7. Brauch S., van Berkela S. S., Westermann B., Chem. Soc. Rev., 2013, 42(12), 4948

    Article  CAS  Google Scholar 

  8. Wang H. J., Mo L. P., Zhang Z. H., J. Comb. Chem., 2011, 13(2), 181

    CAS  Google Scholar 

  9. Yao C., Lei S., Wang C., Li T., Yu C., Wang X., Tu S., J. Heterocycl. Chem., 2010, 47(1), 26

    CAS  Google Scholar 

  10. Medvedev A., Igosheva N., Crumeyrolle-A. M., Glover V., Stress, 2005, 8(3), 175

    Article  CAS  Google Scholar 

  11. Medvedev A., Buneeva O., Glover V., Biologics, 2007, 1(2), 151

    CAS  Google Scholar 

  12. Pandeya S. N., Smitha, S., Jyoti M., Sridhar S. K., Acta Pharm., 2005, 55(1), 27

    CAS  Google Scholar 

  13. Pandeya S. N., Yogeeswari P., Sriram D., De Clercq E., Pannecouque C., Witvrouw M., Chemotherapy, 1999, 45(3), 192

    Article  CAS  Google Scholar 

  14. Tarek A. F., Bin-Jubair F. A. S., Int. J. Res. Pharm. Sci., 2010, 1(2), 113

    CAS  Google Scholar 

  15. Chiyanzu I., Clarkson C., Smith P. J., Lehman J., Rosenthal P. J., Chibale K., Bioorg. Med. Chem., 2005, 13(9), 3249

    Article  CAS  Google Scholar 

  16. Verma M., Pandeya S. N., Singh K. N., Stables J. P., Acta Pharm., 2004, 54(1), 49

    CAS  Google Scholar 

  17. Pandeya S. N., Sriram D., Nath G., De Clercq E., Farmaco., 1999, 54(9), 624

    Article  CAS  Google Scholar 

  18. Holla B. S., Rao B. S., Shridhara K., Akbaerali P. M., Farmaco., 2000, 55(5), 388

    Google Scholar 

  19. Bhamaria R. P., Bellare R. A., Deliwala C. V., Indian J. Exp. Biol., 1968, 6(1), 62

    CAS  Google Scholar 

  20. Pandey S. N., Smitha S., Stables J. P., Arch. Pharm. Pharm. Med. Chem., 2002, 335(4), 129

    Article  Google Scholar 

  21. Cerchiaro G., da Costa Ferreira A. M., J. Braz. Chem. Soc., 2006, 17(8), 1473

    Article  CAS  Google Scholar 

  22. Da Silva J. F. M., Garden S. J., Pinto A. C., J Braz. Chem. Soc., 2001, 12(3), 273

    Article  Google Scholar 

  23. Yamaguchi Y., Clin. Chem., 1978, 24(12), 2178

    CAS  Google Scholar 

  24. Broadhurst A. V., Roberts N. A., Ritchie A. J., Handa B. K., Kay C., Anal. Biochem., 1991, 193(2), 280

    Article  CAS  Google Scholar 

  25. Bonte W., Johansson J., Garbe G., Berg S., Arch. Kriminol., 1976, 158(5/6), 163

    CAS  Google Scholar 

  26. 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

    Article  Google Scholar 

  27. Hutchinson I., Jennings S. A., Vishnuvajjala B. R., Westwell A. D., Stevens M. F. G., J. Med. Chem., 2002, 45(3), 744

    Article  CAS  Google Scholar 

  28. Kalkhambkar R. G., Kulkarni G. M., Shivkumar H., Rao R. N., Eur. J. Med. Chem., 2007, 42(10), 1272

    Article  CAS  Google Scholar 

  29. Kulkarni M. V., Kulkarni G. M., Lin C. H., Sun C. M., Curr. Med. Chem., 2006, 13(23), 2795

    Article  CAS  Google Scholar 

  30. Rajeswar R. V., Padmanabha R. T. V., Indian J. Chem., 1986, 25B(4), 413

    Google Scholar 

  31. 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

    Article  CAS  Google Scholar 

  32. Daka K. S., Chaudhary H. S., Sharma K. S., Pujari H. K., Indian J. Chem., 1976, 14B(5), 541

    Google Scholar 

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Correspondence to Rajeswar Rao Vedula.

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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

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  • DOI: https://doi.org/10.1007/s40242-014-4036-8

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