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Convenient and sequential one-pot route for synthesis of 2-thioxoquinazolinone and quinazolinobenzothiazinedione derivatives

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Abstract

A new and efficient synthetic process has been developed for preparation of 2-thioxoquinazolinone and quinazolinobenzothiazinedione derivatives. The related products were synthesized through reaction of isatoic anhydride, amines/anthranilic acids, and carbon disulfide (CS2) in the presence of potassium hydroxide in ethanol at reflux.

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References

  1. Xia Y, Yang ZY, Hour MJ, Kuo SC, Xia P, Bastow KF, Nakanishi Y, Nampoothiri P, Hackl T, Hamel E, Lee KH (2001) Bioorg Med Chem Lett 11:193

    Article  Google Scholar 

  2. Mukerji DD, Agarwal VR, Nautiyal SR (1985) Indian J Pharm Sci 47:8

    CAS  Google Scholar 

  3. Kenichi O, Yoshihisa Y, Toyonari O, Toru I, Yoshio I (1985) J Med Chem 28:568

    Article  Google Scholar 

  4. Jiang JB, Hesson DP, Dusak BA, Dexter DL, Kang GJ, Hamel E (1990) J Med Chem 33:1721

    Article  CAS  Google Scholar 

  5. Rajasekaran A, Rajamanickam V, Darlinquine S (2001) Yakugaku Zasshi 131:1079

    Article  Google Scholar 

  6. Suesse M, Cleve D, Johne S (1990) Preparation of (3-alkoxycarbonylalkyl-3,4-dihydro-4-oxo-quinazolin-2-ylthio)alkanoic acids and esters as plant growth regulators and fungicides. Ger (East) DD 278788, May 16

  7. Suesse M, Cleve D, Johne S (1991) Chem Abstr 114:62116y

    Google Scholar 

  8. Suesse M, Schaks A, Johne S (1990) Preparation of [(2-alkoxycarbonylalkylthio-3,4-dihydro-4-oxo-quinazolin-3-yl)alkanoyloxy]alkanoic acid esters as plant growth regulators and fungicides. Ger (East) DD 278789, May 16

  9. Suesse M, Schaks A, Johne S (1991) Chem Abstr 114:62115

    Google Scholar 

  10. Lemaire C, Cantineau R, Guillaume M, Plenevaux A, Christiaens L (1991) J Nucl Med 32:2266

    CAS  Google Scholar 

  11. Saeed A, Shaheen U, Bolte M (2010) J Chin Chem Soc 57:82

    CAS  Google Scholar 

  12. Saeed A, Flörke U (2011) Crystals 1:254

    Article  CAS  Google Scholar 

  13. Tiwari VK, Singh DD, Hussain HA, Mishra BB, Singh A (2008) Monatsh Chem 139:43

    Article  CAS  Google Scholar 

  14. Dou GL, Wang MM, Huang ZB, Shi DQ (2009) J Heterocycl Chem 46:645

    Article  CAS  Google Scholar 

  15. Castro A, Jerez MJ, Gil C, Calderón F, Doménech T, Nueda A, Martínez A (2008) Eur J Med Chem 43:1349

    Article  CAS  Google Scholar 

  16. Azizian J, Mohammadi AA, Karimi AR (2003) Synth Commun 33:415

    Article  CAS  Google Scholar 

  17. Satponth PS, Trivedi JP (1971) J Indian Chem Soc 48:1021

    Google Scholar 

  18. Lakhan R, Srivastava M (1993) Proc Indian Acad Sci Chem Sci 105:11

    CAS  Google Scholar 

  19. Singh S, Kaur S, Kaushal AN (1976) J Indian Chem Soc 53:382

    CAS  Google Scholar 

  20. Mahdavi M, Asadi M, Saeedi M, Rezaei Z, Moghbel H, Foroumadi A, Shafiee A (2012) Synlett 23:2521

    Article  CAS  Google Scholar 

  21. Hosseini-Zare MS, Mahdavi M, Saeedi M, Asadi M, Javanshir S, Shafiee A, Foroumadi A (2012) Tetrahedron Lett 53:3448

    Article  CAS  Google Scholar 

  22. Mahdavi M, Asadi M, Saeedi M, Ebrahimi M, Rasouli MA, Ranjbar PR, Foroumadi A, Shafiee A (2012) Synthesis 44:3649

    Article  CAS  Google Scholar 

  23. Tahghighi A, Razmi S, Mahdavi M, Foroumadi P, Ardestani SK, Emami S, Kobarfard F, Dastmalchi S, Shafiee A, Foroumadi A (2012) Eur J Med Chem 50:124

    Article  CAS  Google Scholar 

  24. Khalaj A, Nakhjiri M, Negahbani AS, Samadizadeh M, Firoozpour L, Rajabalian S, Samadi N, Faramarzi MA, Adipour N, Shafiee A, Foroumadi A (2011) Eur J Med Chem 46:65

    Article  CAS  Google Scholar 

  25. Sunder S, Peet NP (1979) J Heterocycl Chem 16:1339

    Article  CAS  Google Scholar 

  26. Wang M, Zhang TT, Liang Y, Gao JJ (2012) Monatsh Chem 143:835

    Article  CAS  Google Scholar 

  27. Karimi-Jaberi Z, Arjmandi R (2011) Monatsh Chem 142:631

    Article  CAS  Google Scholar 

  28. Mahdavi M, Asadi M, Saeedi M, Tehrani MH, Mirfazli SS, Shafiee A, Foroumadi A (2013) Synth Commun 43:2936

    Article  CAS  Google Scholar 

  29. Clark RH, Wagner EC (1944) J Org Chem 9:55

    Article  CAS  Google Scholar 

  30. Staiger RP, Wagner EC (1948) J Org Chem 13:347

    Article  CAS  Google Scholar 

  31. Staiger RP, Miller EB (1959) J Org Chem 24:1214

    Article  CAS  Google Scholar 

  32. Talukdar PB, Sengupta SK, Datta AK, Roy TK (1977) Indian J Chem B 15B:41

    Google Scholar 

  33. Wagner G, Rothe L (1969) Pharmazie 24:513

    CAS  Google Scholar 

  34. Shafik RM, Hazzaa AAB, Habib NS (1979) Pharmazie 34:148

    CAS  Google Scholar 

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Acknowledgments

We gratefully acknowledge the partial financial support from Tehran University of Medicinal Sciences Research Council and Iran National Science Foundation (INSF).

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Authors and Affiliations

  1. School of Chemistry, University College of Science, University of Tehran, PO Box 14155-6455, Tehran, Iran

    Mehdi Asadi

  2. Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medicinal Sciences, Tehran, Iran

    Shiva Masoomi, Seyed Mostafa Ebrahimi, Mohammad Mahdavi, Mina Saeedi, Abbas Shafiee & Alireza Foroumadi

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  1. Mehdi Asadi
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  2. Shiva Masoomi
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  3. Seyed Mostafa Ebrahimi
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  4. Mohammad Mahdavi
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  5. Mina Saeedi
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  6. Abbas Shafiee
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  7. Alireza Foroumadi
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Corresponding author

Correspondence to Alireza Foroumadi.

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Asadi, M., Masoomi, S., Ebrahimi, S.M. et al. Convenient and sequential one-pot route for synthesis of 2-thioxoquinazolinone and quinazolinobenzothiazinedione derivatives. Monatsh Chem 145, 497–504 (2014). https://doi.org/10.1007/s00706-013-1110-8

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  • DOI: https://doi.org/10.1007/s00706-013-1110-8

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