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Novel synthesis of dihydroquinoxaline, thiocyanatomaleate, uracil, pyridinium ylide, and S-aryl carbamimidothioate derivatives

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Abstract

The novel functionalized alkyl (Z)-2-(3-oxo-3,4-dihydroquinoxalin-2(1H)-ylidene)acetate, uracil, and thiocyanatomaleate derivatives have been prepared from substituted dihydroquinoxalines, benzylaminomaleates, and 6-amino-1,3-dimethylpyrimidine-2,4(1H,3H)-dione in the presence of N-thiocyanatosuccinimide intermediate generated from NH4SCN with NCS at room temperature, respectively. Convenient synthesis of sulfur-containing compounds of pyridinium ylide and S-aryl carbamimidothioate derivatives is described under catalyst-free condition in good yields.

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References

  1. Promkatkaew M, Gleeson D, Hannongbua S, Gleeson MP (2014) Chem Res Toxicol 27:240

    Article  Google Scholar 

  2. Yasman Y, Edrada RA, Wray V, Proksch P (2003) J Nat Prod 66:1512

    Article  CAS  PubMed  Google Scholar 

  3. Elhalem E, Bailey BN, Docampo R, Ujvary I, Szajnman SH, Rodriguez HB (2002) J Med Chem 45:3984

    Article  CAS  PubMed  Google Scholar 

  4. Mukerjee AK, Ashare R (1991) Chem Rev 91:1

    Article  CAS  Google Scholar 

  5. Nedly NA, Trofimov BA, Senning A (1996) Sulfur Rep 17:183

    Article  Google Scholar 

  6. Sommen G (2004) Synlett 7:1323

    Article  Google Scholar 

  7. Grant MS, Snyder HR (1960) J Am Chem Soc 82:2742

    Article  CAS  Google Scholar 

  8. Toaste FD, Laronde F, Still WJ (1995) Tetrahedron Lett 36:2949

    Article  Google Scholar 

  9. Reeves WP, McClusky JV (1983) Tetrahedron Lett 24:1585

    Article  CAS  Google Scholar 

  10. Kiasat AR, Faiiah-Mehrjardi M (2008) Bull Korean Chem Soc 29:2346

    Article  CAS  Google Scholar 

  11. Kamal A, Chouhan G (2005) Tetrahedron Lett 46:1489

    Article  CAS  Google Scholar 

  12. Guram AS (1993) Synlett 4:259

    Article  Google Scholar 

  13. Ando T, Clark JH, Cork DG, Fujita M, Kimura T (1987) J Org Chem 52:681

    Article  CAS  Google Scholar 

  14. Iranpoor N, Firouzabadi H, Azadi R, Akhlaghinia B (2005) J Sulfur Chem 26:133

    Article  CAS  Google Scholar 

  15. Ashby MT, Areetha H (2004) J Am Chem Soc 126:10216

    Article  CAS  PubMed  Google Scholar 

  16. Falck JR, Gao SH, Prasad RN, Koduru SR (2008) Bioorg Med Chem Lett 18:1768

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  17. Firouzabadi H, Iranpoor N, Garzan A, Shaterian HR, Ebrahimzadeh F (2005) Eur J Org Chem 2005:416

    Article  Google Scholar 

  18. Toste FD, De Stefano V, Still WJ (1995) Synth Commun 25:1277

    Article  CAS  Google Scholar 

  19. Avalos M, Babiano R, Chintas P, Jimenez JL, Palacios JC (1992) Heterocycles 33:973

    Article  CAS  Google Scholar 

  20. Mamedov VA (2016) Quinoxalines: synthesis reactions, mechanisms and structure. Springer, Switzerland

    Book  Google Scholar 

  21. Khalili G (2016) Mol Diversity 20:963

    Article  CAS  Google Scholar 

  22. Agarwal N, Raghuwanshi SK, Upadhyay DN, Shukla PK, Ram VJ (2000) Bioorg Med Chem Lett 10:703

    Article  CAS  PubMed  Google Scholar 

  23. Sasada T, Kobayashi F, Sakai N, Konakahara T (2009) Org Lett 11:2161

    Article  CAS  PubMed  Google Scholar 

  24. Lee HW, Bok YK, Joong BA (2005) Eur J Med Chem 40:862

    Article  CAS  PubMed  Google Scholar 

  25. Hasheni SA, Khalili G (2015) Synth Commun 45:2491

    Article  Google Scholar 

  26. Khalili G (2015) Monatsh Chem 146:1891

    Article  CAS  Google Scholar 

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Acknowledgements

We thank the Bushehr Branch, Islamic Azad University for support.

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Correspondence to Gholamhossein Khalili.

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Monfared, A., Khalili, G. Novel synthesis of dihydroquinoxaline, thiocyanatomaleate, uracil, pyridinium ylide, and S-aryl carbamimidothioate derivatives. Monatsh Chem 153, 1235–1241 (2022). https://doi.org/10.1007/s00706-022-02992-y

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  • DOI: https://doi.org/10.1007/s00706-022-02992-y

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