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4-Amino and 5-aminobenzothiadiazoles in Gould–Jacobs reaction

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Abstract

4-Amino and 5-aminobenzothiadiazoles were prepared and submitted to reaction with activated enolethers to prepare N-substituted benzothiadiazolylaminoethylene derivatives. Selected aminoethylenes were thermally cyclized to angularly annelated thiadiazolylaminoethylene under Gould–Jacobs reaction conditions. Prepared products were modified to obtain variously substituted thiadiazoloquinolones.

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References

  1. Norris S, Mandell GL (1988) The quinolones: history and overview. In: The quinolones: history and overview. Academic Press Inc, San Diego, p 1

  2. Heeb S, Fletcher MP, Chabra SR, Diggle SP, Williams P, Cámara M (2011) FEMS Microbiol Rev 35:247

    Article  CAS  PubMed  Google Scholar 

  3. Milata V, Claramunt RM, Elguero J, Zálupský P (2000) Targets Heterocycl Syst 4:167

    CAS  Google Scholar 

  4. Sorbera LA, Serradel N (2006) Drugs Future 31:310

    Article  CAS  Google Scholar 

  5. Li JJ (ed) (2004) Name reactions in heterocyclic chemistry. Wiley, Hoboken, p 423

    Google Scholar 

  6. Li JJ (2009) Gould-Jacobs reaction. In: Name reactions: a collection of detailed mechanisms and synthetic applications, 4th edn. Springer, Berlin, Heidelberg, pp 263-265

  7. Al-Qawasmeh RA, Zahra JA, Zani F, Vicini P, Boese R, El-Abadelah MM (2009) Arkivoc 12:322

    Google Scholar 

  8. Al-Qawasmeh RA, Abadleh MM, Zahra JA, El-Abadelah MM, Albashiti R, Zani F, Incerti M, Vicini P (2014) J Enzyme Inhib Med Chem 29:777

    Article  CAS  PubMed  Google Scholar 

  9. Milata V, Ilavský D (1987) Coll Czech Chem Commun 52:2918

    Article  CAS  Google Scholar 

  10. Bella M, Schulz M, Milata V, Koňariková K, Breza M (2010) Tetrahedron 66:8169

    Article  CAS  Google Scholar 

  11. Bella M, Schultz M, Milata V (2012) Arkivoc 4:242

    Google Scholar 

  12. Saloň J, Milata V, Prónayová N, Leško J (2000) Monatsh Chem 131:293

    Article  Google Scholar 

  13. Saloň J, Milata V, Prónayová N, Leško J (2001) Collect Czech Chem Commun 66:1691

    Article  Google Scholar 

  14. Saloň J, Milata V, Chudík M, Prónayová N, Leško J, Seman M, Belicová A (2004) Monatsh Chem 135:283

    Article  CAS  Google Scholar 

  15. Wąsik R, Wińska P, Poznański J, Shugar D (2012) J Phys Chem B 116:7259

    Article  CAS  PubMed  Google Scholar 

  16. Liu Y, Lu Y, Prashad M, Repič O, Blacklock TJ (2005) Adv Synth Catal 347:217

    Article  CAS  Google Scholar 

  17. Saloň J, Milata V, Gatial A, Prónayová N, Leško J, Černuchová P, Vo-Thanh G, Loupy A (2005) Eur J Org Chem 22:4870

    Article  Google Scholar 

  18. Couchouron B, Le Saint J, Courtot P (1983) Bull Soc Chim Fr II(3–4):66

    Google Scholar 

  19. Milata V, Ilavský D, Goljer I, Leško J, Chahinian M, Henry-Basch E (1990) Coll Czech Chem Commun 55:1038

    Article  CAS  Google Scholar 

  20. Goljer I, Milata V, Ilavský D (1989) Magn Reson Chem 27:138

    Article  CAS  Google Scholar 

  21. Bobošík V, Milata V, Ilavský D, Goljer I (1992) Coll Czech Chem Commun 57:397

    Article  Google Scholar 

  22. Milata V, Ilavský D, Chudík M (1995) Monatsh Chem 126:1349

    Article  CAS  Google Scholar 

  23. Zalibera Ľ, Milata V, Ilavský D (1998) Magn Reson Chem 36:681

    Article  CAS  Google Scholar 

  24. Katritzky AR, Ellison J, Frank J, Rákóczy P, Radics L, Gács-Baitz E (1981) Org Magn Reson 16:280

    Article  CAS  Google Scholar 

  25. Devlin TA, Jebaratnam DJ (1995) Synth Commun 25:711

    Article  CAS  Google Scholar 

  26. Tobiason FL, Huestis L, Chandler C, Pedersen SE, Peters P (1973) J Heterocycl Chem 10:773

    Article  CAS  Google Scholar 

  27. Liu Y, Lu Y, Prashad M, Repic O, Blacklock TJ (2005) Adv Synth Catal 2–3:217

    Article  CAS  Google Scholar 

  28. Efros LS (1955) Zh Obsch Khim 25:199

    CAS  Google Scholar 

  29. Mikhailitsyn FS, Bekhli AF (1976) Khim Geterotsikl Soed 1:61

    Google Scholar 

  30. Ohmori J, Sakamoto S, Kupota H, Shimizu-Sasamata M, Okada M, Kawasaki S, Hidaka K, Togami J, Furuya T, Midase K (1994) J Med Chem 37:467

    Article  CAS  PubMed  Google Scholar 

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Acknowledgements

This work was supported by the Slovak Research and Development Agency under the contract no. APVV-17-0513.

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Correspondence to Viktor Milata.

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Milata, V., Vaculka, M. 4-Amino and 5-aminobenzothiadiazoles in Gould–Jacobs reaction. Monatsh Chem 150, 711–719 (2019). https://doi.org/10.1007/s00706-019-2378-0

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  • DOI: https://doi.org/10.1007/s00706-019-2378-0

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