Skip to main content
Log in

A ring opening reaction of 2-hetaryl-2-(tetrahydro-2-furanylidene)acetonitriles with amino acids

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

Abstract

The ring opening reactions of 2-hetaryl-2-(tetrahydro-2-furanylidene)acetonitriles with α-, β-, γ-, ε-amino acids and alkyl esters of α-amino acids as N-nucleophiles have been investigated. New functionalized amino acid derivatives containing the heterocyclic moiety have been obtained and their reactions with electrophilic and nucleophilic agents have been studied.

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.

Fig. 1

Similar content being viewed by others

References

  1. Hetch S (1998) Bioorganic chemistry: peptides and proteins. Oxford University Press, Oxford

    Google Scholar 

  2. Gringauz A (1997) Introduction to medicinal chemistry: how drugs act and why. Wiley-VCH, New York

    Google Scholar 

  3. Collins AN, Sheldrake GN, Crosby J (1992) Chirality in industry: the commercial manufacture and applications of optically active compounds. Wiley, Chichester

    Google Scholar 

  4. Wagner I, Musso H (1983) Angew Chem Int Ed 22:816

    Article  Google Scholar 

  5. Takahashi Y, Kubota T, Fromont J, Kobayashi J (2007) Tetrahedron 63:8770

    Article  CAS  Google Scholar 

  6. Sardina FJ, Rapoport H (1996) Chem Rev 96:1825

    Article  CAS  Google Scholar 

  7. Coppola GM, Schuster HF (1987) Asymmetric synthesis: construction of chiral molecules using amino acids. Wiley, New York

    Google Scholar 

  8. Reetz MT (1991) Angew Chem Int Ed 30:1531

    Article  Google Scholar 

  9. Cheng RP, Gellman SH, DeGrado WF (2001) Chem Rev 101:3219

    Article  CAS  Google Scholar 

  10. Porter EA, Wang X, Lee H, Weisblum B, Gellman SH (2000) Nature 404:565

    Article  CAS  Google Scholar 

  11. Koert U (1997) Angew Chem Int Ed 36:1836

    Article  CAS  Google Scholar 

  12. Alcaide B, Almendros P, Aragoncillo C (2007) Chem Rev 107:4437

    Article  CAS  Google Scholar 

  13. Shinada T, Ishida T, Hayashi K, Yoshida Y, Shigeri Y, Ohfune Y (2007) Tetrahedron Lett 48:7614

    Article  CAS  Google Scholar 

  14. Onaran MB, Comeau AB, Seto CT (2005) J Org Chem 70:10792

    Article  CAS  Google Scholar 

  15. Sejwal P, Han Y, Shah A, Luk Y (2007) Org Lett 9:4897

    Article  CAS  Google Scholar 

  16. Pätzel M, Liebscher J (1995) Synthesis 879

  17. Batra S, De D, Seth M, Bhaduri AP (1993) J Chem Res (Synop) 6:202

    Google Scholar 

  18. Pätzel M, Liebscher J (1991) J Heterocycl Chem 28:1257

    Article  Google Scholar 

  19. Detty MR (1979) J Org Chem 44:2073

    Article  CAS  Google Scholar 

  20. Bellur E, Langer P (2006) Tetrahedron 62:5426

    Article  CAS  Google Scholar 

  21. Volovenko YuM, Khilya OV, Volovnenko TA (2003) In: Kartsev VG (ed), Oxygen- and sulfur-containing heterocycles. IBS PRESS, Moscow

  22. Khilya OV, Volovnenko TA, Turov AV, Zubatyuk RI, Shishkin OV, Volovenko YuM (2012) Khim Geterotsikl Soedin 12:1891

    Google Scholar 

  23. Milokhov DS, Khilya OV, Volovenko YuM, Palamarchuk GV, Shishkin OV (2012) Synlett 23:2063

    Google Scholar 

  24. Volovenko YuM, Khilya OV, Volovnenko TA (2003) Chem Heterocycl Compd (Engl Transl) 39:394

    Google Scholar 

  25. Khilya OV, Volovnenko TA, Turov AV, Zubatyuk RI, Shishkin OV, Volovenko YuM (2011) Chem Heterocycl Compd (Engl Transl) 47:1141

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to O. V. Khilya.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Khilya, O.V., Milokhov, D.S., Postupalenko, V.Y. et al. A ring opening reaction of 2-hetaryl-2-(tetrahydro-2-furanylidene)acetonitriles with amino acids. Monatsh Chem 144, 1071–1079 (2013). https://doi.org/10.1007/s00706-013-0967-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-013-0967-x

Keywords

Navigation