Skip to main content
Log in

Synthesis of 2-thioxo-4,6-diphenyl-1,2-dihydronicotinonitrile via condensation of benzaldehyde with cyanothioacetamide and p-(1-styryl)morpholine

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

2-Thioxo-4,6-diphenyl-1,2-dihydronicotinonitrile has been prepared via condensation of benzaldehyde with cyanothioacetamide and N-(1-styryl)morpholine; alkylation of the product with alkyl halides has afforded substituted 2-alkylsulfanyl-4,6-diphenylnicotinonitriles and 3-amino-2-acyl-4,6-diphenylthieno[2,3-b]pyridines.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Mohamed, S.F., Youssef, M.H., Amr, A.E.-G., and Kotb, E.R., Scipharm., 2008, vol. 76, no. 2, p. 279. DOI: 10.3797/scipharm.0804-09.

    CAS  Google Scholar 

  2. Abdulla, M.M., Monatsh. Chem., 2008, vol. 139, no. 6, p. 697. DOI: 10.1007/s00706-007-0804-1.

    Article  CAS  Google Scholar 

  3. US Patent 6184237, 2001; Ref. Zh. Khim., 2002, 02.04-19O.86P.

  4. Germany Patent 10130357 2003; Ref. Zh. Khim., 2003. 03.18-19O.347P.

  5. Krauze, A.A., Bomika, Z.A., Shestopalov, A.M., Rodinovskaya, L.A., Pelcher, Yu.É., Dubur, G.Ya., Sharanin, Yu.A., and Promonenkov, V.K., Chem. Heterocycl. Compd., 1981, vol. 17, no. 3, p. 279. DOI: 10.1007/BF00505994.

    Article  Google Scholar 

  6. Shestopalov, A.M., Promonenkov, V.K., Sharanin, Yu.A., Rodinovskaya, L.A., and Sharanin, S.Yu., Zh. Org. Khim., 1984, vol. 20, no. 7, p. 1517.

    CAS  Google Scholar 

  7. Krauze, A.A., Kalme, Z.A., Pelcher, Yu.É., Liepin’sh, É.É., Dipan, I.V., and Dubur, G.Ya., Chem. Heterocycl. Compd., 1983. vol. 19, no. 11, p. 1202. DOI: 10.1007/BF00515357.

    Article  Google Scholar 

  8. Abdel-Fattah, A.M., Elneairy, M.A.A., Gouda, M.N., and Attaby, F.A., Phosphorus, Sulfur, Silicon, Relat. Elem., 2008, vol. 183, no. 7, p. 1592. DOI: 10.1080/10426500701693552.

    Article  CAS  Google Scholar 

  9. Elgemeie, G.E.H., Elfohnan, H.A., and Nabey, H.A., Sulfur Lett., 1989, vol. 9, nos. 1–2, p. 47.

    CAS  Google Scholar 

  10. Abdel-Rahman, A.E., Bakhite, E.A., Mohamed, O.S., and Thabet, E.A., Phosphorus, Sulfur, Silicon, Relat. Elem., 2003, vol. 178, no. 1, p. 89. DOI: 10.1080/10426500307820.

    Article  CAS  Google Scholar 

  11. Promonenkov, V.K., Shestopalov, A.M., Sharanin, Yu.A., Litvinov, V.P., Rodinovskaya, L.P., Zolotarev, B.M., Sokovykh, V.D., Rozynov, B.V., and Krymskii, Ya.Ya., Zh. Org. Khim., 1985, vol. 21, no. 9, p. 1963.

    CAS  Google Scholar 

  12. Dyachenko, V.D., Russ. J. Org. Chem., 2011, vol. 47, no. 10, p. 1535. DOI: 10.1134/S1070428011100150.

    Article  CAS  Google Scholar 

  13. Dyachenko, V.D., Chem. Heterocycl. Compd., 2005, vol. 41, no. 8, p. 1005. DOI: 10.1007/s10593-005-0268-3.

    Article  CAS  Google Scholar 

  14. Dyachenko, V.D. and Chernega, A.N., Chem. Heterocycl. Compd., 2005, vol. 41, no. 12, p. 1499. DOI: 10.1007/s10593-006-0027-0.

    Article  CAS  Google Scholar 

  15. Stork, G., Brizzolara, A., Landesman, H., Szmuszkovich, J., and Terrell, R., J. Am. Chem. Soc., 1963, vol. 85, no. 2, p. 207. DOI: 10.1021/ja00885a021.

    Article  CAS  Google Scholar 

  16. Mishchenko, G.L. and Vatsuro, K.V., Sinteticheskie metody organicheskoi khimii (Synthetic Methods of Organic Chemistry), Moscow: Khimiya, 1982, p. 297.

    Google Scholar 

  17. EP Patent EP 1683799, 2006; Ref. Zh. Khim., 2007, 07.20-19O.115P.

  18. US Patent US 6964956, 2005; Ref. Zh. Khim., 2006, 06.14-19O.69P.

  19. EP Patent EP 1681292, 2006; Ref. Zh. Khim., 2007, 07.20-19O.116P.

  20. Pretsch, E., Biihlmann, P., and Affolter, C., Structure Determination of Organic Compounds, Berlin: Springer, 2000.

    Book  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to I. V. Dyachenko.

Additional information

Original Russian Text © I.V. Dyachenko, V.D. Dyachenko, 2015, published in Zhurnal Obshchei Khimii, 2015, Vol. 85, No. 6, pp. 980–984.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Dyachenko, I.V., Dyachenko, V.D. Synthesis of 2-thioxo-4,6-diphenyl-1,2-dihydronicotinonitrile via condensation of benzaldehyde with cyanothioacetamide and p-(1-styryl)morpholine. Russ J Gen Chem 85, 1447–1451 (2015). https://doi.org/10.1134/S1070363215060146

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363215060146

Keywords

Navigation