Skip to main content
Log in

Ph3P-mediated one-pot synthesis of functionalized 3,4-dihydro-2H-1,3-thiazines from N,N′-dialkylthioureas and activated acetylenes in water

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

A one-pot synthesis of alkyl 3,4-dihydro-4-oxo-2H-1,3-thiazine-6-carboxylates from dialkyl acetylenedicarboxylates and N,N′-dialkylthioureas in the presence of triphenylphosphine (20 mol%) is described.

Graphical Abstract

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.

Scheme 1
Scheme 2

Similar content being viewed by others

References

  1. Patel HS, Patel NP (1997) Orient J Chem 13:69

    CAS  Google Scholar 

  2. Madkour HMF, Salem MAI, Soliman EA, Mahmoud NFH (2001) Phosphorus Sulfur Silicon Relat Elem 170:15

    Article  CAS  Google Scholar 

  3. Ingarsal N, Amutha P, Nagarajan S (2006) J Sulfur Chem 27:455

    Article  CAS  Google Scholar 

  4. Bozsing D, Sohar P, Gigler G, Kovacs G (1996) Eur J Med Chem 31:663

    Article  CAS  Google Scholar 

  5. Tozkoparan B, Aktay G, Yeilada E (2002) Il Farmaco 57:145

    Article  CAS  Google Scholar 

  6. Campaigne E, Nargund PK (1964) J Org Chem 29:224

    Article  CAS  Google Scholar 

  7. Barret GC, Kane VV, Lowe G (1964) J Chem Soc 783

  8. Schmidt RR (1972) Synthesis 333

  9. Yuskovets VN, Ivin BA (2003) Tetrahedron Lett 44:5279

    Article  CAS  Google Scholar 

  10. Yadav LDS, Sharma S (1992) Synthesis 919

  11. Yadav LDS, Yadav DS (1995) Liebigs Ann Chem 2231

  12. Yadav LDS, Shukla S, Saigal S (1996) Indian J Chem 35B:102

    CAS  Google Scholar 

  13. Noshio T, Konno Y, Ori M, Sakamoto M (2001) Eur J Org Chem 3533

  14. Koketsu M, Tanaka K, Takenaka Y, Kwong CD, Ishihara H (2002) Eur J Pharm Sci 15:307

    Article  CAS  Google Scholar 

  15. Yadav LDS, Singh S (2003) Indian J Chem 42B:1115

    CAS  Google Scholar 

  16. Murai T, Niwa H, Kimura T, Shibahara F (2004) Chem Lett 33:508

    Article  CAS  Google Scholar 

  17. Yadav LDS, Singh A (2004) Tetrahedron Lett 44:5637

    Article  Google Scholar 

  18. Huang S, Pan Y, Zhu Y, Wu A (2005) Org Lett 7:3797

    Article  CAS  Google Scholar 

  19. Yadav LDS, Patel R, Rai VK, Srivastava VP (2007) Tetrahedron Lett 48:7793

    Article  CAS  Google Scholar 

  20. Rasovic A, Steel PJ, Kleinpeter E, Markovic R (2007) Tetrahedron 63:1937

    Article  CAS  Google Scholar 

  21. Ashraf AA, Ahmed EK, El-Mokadam KM (2007) J Heterocycl Chem 44:1431

    Google Scholar 

  22. Darehkordi A, Saidi K, Islami MR (2007) Arkivoc (i):180

    Google Scholar 

  23. Grieco PA (1998) Organic synthesis in water. Blackie Academic & Professional, Glasgow

    Google Scholar 

  24. Anastas P, Williamson TC (1998) Green chemistry frontiers in benign chemical synthesis and processes. Oxford University Press, New York

    Google Scholar 

  25. Yavari I, Hosseini N, Moradi L (2008) Monatsh Chem 139:133

    Article  CAS  Google Scholar 

  26. Yavari I, Zare H (2007) Monatsh Chem 138:787

    Article  CAS  Google Scholar 

  27. Yavari I, Hossaini Z, Sabbaghan M, Ghazanfarpour-Darjani M (2007) Monatsh Chem 138:677

    Article  CAS  Google Scholar 

  28. Zaitsev AB, Vasil’tsov AM, Schmidt EYu, Mikhaleva AI, Morozova LV, Afonin AV, Ushakov IA, Trofimov BA (2002) Tetrahedron 58:10043

    Article  CAS  Google Scholar 

  29. Wilson K, Adams DJ, Rothenberg G, Clark JH (2002) J Mol Catal A Chem 159:309

    Article  Google Scholar 

  30. Trost BM, Dake GR (1997) J Am Chem Soc 119:7595

    Article  CAS  Google Scholar 

  31. Trost BM, Kazmaier U (1992) J Am Chem Soc 114:7933

    Article  CAS  Google Scholar 

  32. Trost BM, Li C (1994) J Am Chem Soc 116:3167

    Article  CAS  Google Scholar 

  33. Rafel S, Leahy JW (1997) J Org Chem 62:1521

    Article  CAS  Google Scholar 

  34. Yavari I, Ramazani A (1997) Synth Commun 27:1449

    Article  CAS  Google Scholar 

  35. Yavari I, Norouzi-Arasi H (2002) Phosphorus Sulfur Silicon Relat Elem 177:87

    Article  CAS  Google Scholar 

  36. Yavari I, Souri S, Sirouspour M, Djahaniani H, Nasiri F (2005) Synthesis 1761

  37. Yavari I, Hazeri N, Maghsoodlou MT, Souri S (2007) J Mol Catal A Chem 264:313

    Article  CAS  Google Scholar 

  38. Bhuvan Kumar NN, Kumara Swamy KC (2008) Tetrahedron Lett 49:7135

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Issa Yavari.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Yavari, I., Nematpour, M. & Hossaini, Z. Ph3P-mediated one-pot synthesis of functionalized 3,4-dihydro-2H-1,3-thiazines from N,N′-dialkylthioureas and activated acetylenes in water. Monatsh Chem 141, 229–232 (2010). https://doi.org/10.1007/s00706-009-0247-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-009-0247-y

Keywords

Navigation