Skip to main content

Advertisement

SpringerLink
Log in

Cyclic α-amino acids as precursors for synthesis of 2-amino-3-hetarylpyrrolin-4-ones and their spiro derivatives

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

Abstract

α-Aminoisobutanoic acid and some representatives of cyclic α-amino acids were converted to corresponding 1-phthalimido- and N-trifluoroacylated acid chlorides. Treatment of 2-(1H-benzimidazol-2-yl)acetonitrile with 1-phthalimidoacid chlorides in DMF unexpectedly gave 2-(1H-benzimidazol-2-yl)-3-(dimethylamino)-2-propenenitrile. On the other hand, the reaction of hetarylacetonitriles with N-trifluoroacylated acid chlorides gave the desired (3-cyano-2-oxo-3-hetarylpropyl)-2,2,2-trifluoroacetamides that upon detrifluoroacetylation provided the target 2-amino-3-hetarylpyrrolin-4-ones. The acylation of benzoimidazolylaminopyrrolinones by benzoyl chloride leads to formation of 3-benzoyl-2,3-dihydro-5-phenyl-1H-benzo[4,5]imidazo[1,2-c]pyrrolo[3,2-e]pyrimidin-1-ones.

Graphical Abstract

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Scheme 2
Scheme 3
Scheme 4
Fig. 1

Similar content being viewed by others

References

  1. Tanaka M, Tsuba M, Nakamura A (1999) Pat WO 9936068

  2. Tanaka M, Tsuba M, Nakamura A (1999) Chem Abstr 131:97597

    Google Scholar 

  3. Tsuba M, Tanaka M, Nakamura A (1997) Pat WO 9640634

  4. Tsuba M, Tanaka M, Nakamura A (1997) Chem Abstr 126:117863

    Google Scholar 

  5. Eggenweiler H-M, Jonas R, Wolf M, Gassen M, Welge T (2001) Pat DE 19953025

  6. Eggenweiler H-M, Jonas R, Wolf M, Gassen M, Welge T (2001) Chem Abstr 134:344596

    Google Scholar 

  7. Howard OMZ, Oppenheim JJ, Melinda MG, Covey JM, Bigelow J (1998) J Med Chem 41:2184

    Article  CAS  Google Scholar 

  8. Yaroslavsky C, Bracha P, Glaser R (1989) J Heterocycl Chem 26:1649

    Article  CAS  Google Scholar 

  9. Trani A, Bellasio E (1983) Farmaco 38:940

    CAS  Google Scholar 

  10. Ibrahim MK (1998) Egypt J Pharm Sci 39:519

    CAS  Google Scholar 

  11. Attanasi O, Colombani SM, De Crescentini L, Giorgi R, Monti S, Perrone A, Perrulli FR, Renzetti AR, Santeusanio S (1999) Farmaco 54:64

    Article  CAS  Google Scholar 

  12. Tverdokhlebov AV, Lyashenko AB, Volovenko YuM, Tolmachev AA (2004) Khim Geterotsikl Soedin 12:1783

    Google Scholar 

  13. Tverdokhlebov AV, Lyashenko AB, Volovenko YuM, Tolmachev AA (2004) Chem Heterocycl Compd (Engl Transl) 40:1536

    Google Scholar 

  14. Volovenko YuM (1997) Khim Geterotsikl Soedin 8:975

    Google Scholar 

  15. Volovenko YuM (1997) Chem Heterocycl Compd (Engl Transl) 33:997

    Article  CAS  Google Scholar 

  16. Volovenko YuM, Shokol TV, Babichev FS (1986) Dopov Akad Nauk UK RSR Ser B 2:35

    Google Scholar 

  17. Volovenko YuM, Tverdokhlebov AV, Gorulya AP, Shishkina SV, Zubatyuk RI, Shishkin OV (2002) Eur J Org Chem 663

  18. Tverdokhlebov AV, Volovenko YuM, Shokol TV (1998) Khim Geterotsikl Soedin 1:50

  19. Tverdokhlebov AV, Volovenko YuM, Shokol TV (1998) Chem Heterocycl Compd (Engl Transl) 34:44

    Google Scholar 

  20. Resnyanskaya EV, Shokol TV, Volovenko YuM, Tverdokhlebov AV (1999) Khim Geterotsikl Soedin 10:1412

    Google Scholar 

  21. Resnyanskaya EV, Shokol TV, Volovenko YuM, Tverdokhlebov AV (1999) Chem Heterocycl Compd (Engl Transl) 35:1230

    Google Scholar 

  22. Resnyanskaya EV, Tverdokhlebov AV, Volovenko YuM, Shokol TV (2004) Zh Org Khim 40:398

    Google Scholar 

  23. Resnyanskaya EV, Tverdokhlebov AV, Volovenko YuM, Shokol TV (2004) Russ J Org Chem 40:368

    Article  CAS  Google Scholar 

  24. Eldin AMS (2003) Heteroatom Chem 14:612

    Article  CAS  Google Scholar 

  25. Gewald K, Hentschel M (1976) J Prakt Chem 318:663

    Article  CAS  Google Scholar 

  26. Teuber H-J, Schütz G, Erkenbrecher E (1980) Arch Pharm 313:851

    Article  CAS  Google Scholar 

  27. Dave CG, Shah PR, Upadhyaya SP (1987) J Indian Chem Soc 64:713

    CAS  Google Scholar 

  28. Dave CG, Desai ND (1999) J Heterocycl Chem 36:729

    Article  CAS  Google Scholar 

  29. Volovenko YuM, Volovnenko TA, Tverdokhlebov AV, Ryabokon IG (2001) Zh Org Khim 37:1389

    Google Scholar 

  30. Volovenko YuM, Volovnenko TA, Tverdokhlebov AV, Ryabokon IG (2001) Russ J Org Chem (Engl Transl) 37:1323

    Google Scholar 

  31. Tverdokhlebov AV, Tolmachev AA, Volovenko YuM (2004) Collect Czech Chem Commun 69:414

    Google Scholar 

  32. Volovenko YuM, Resnyanskaya EV, Tverdokhlebov AV (2002) Collect Czech Chem Commun 67:356

    Google Scholar 

  33. Volovenko YuM, Resnyanskaya EV, Tverdokhlebov AV (2002) Khim Geterotsikl Soedin 3:360

  34. Volovenko YuM, Resnyanskaya EV, Tverdokhlebov AV (2002) Chem Heterocycl Compd (Engl Transl) 38:324

  35. Heinrich MR, Zard SZ (2004) Org Lett 26:4969

    Article  Google Scholar 

  36. Moretto A, Zotti MD, Scipionato L, Formaggio F, Crisma M, Toniolo C, Antonello S, Maran F, Broxterman QB (2002) Helv Chim Acta 85:3099

    Article  CAS  Google Scholar 

  37. Al-Hassan SS, Cameron RJ, Curran AWC, Lyall WJS, Nicholson SH, Robinson DR, Stuart A, Suckling CJ, Stirling I, Wood HCS (1985) J Chem Soc Perkin Trans 1:1645

    Article  Google Scholar 

  38. Haddow J, Suckling CJ, Wood HCS (1989) J Chem Soc Perkin Trans 1:1297

    Article  Google Scholar 

  39. Connors TA, Ross WCJ (1960) J Chem Soc 2119

  40. Los M (1977) Pat US 4041045

  41. Los M (1977) Chem Abstr 87:168034

    Google Scholar 

  42. Jones DS, Kenner GW, Sheppard RC (1960) Tetrahedron 11:39

    Article  Google Scholar 

  43. Hickey MR, Nelson TD, Secord EA, Allwein SP, Kress MH (2005) Synlett 2:255

    Article  Google Scholar 

  44. Weygand F, Geiger R (1956) Chem Ber 89:647

    Article  CAS  Google Scholar 

  45. Nordlander JE, Payne MJ, Njoroge FG, Balk MA, Laikos GD, Vishwanath VM (1984) J Org Chem 49:4107

    Article  CAS  Google Scholar 

  46. Schallenberg EF, Calvin M (1955) J Am Chem Soc 77:2779

    Article  CAS  Google Scholar 

  47. Zefirov YV, Zorkii PM (1989) Russ Chem Rev 58:421

    Article  Google Scholar 

  48. Shishkin OV, Gorb L, Lesczynski J (2000) Chem Phys Lett 330:603

    Article  CAS  Google Scholar 

  49. Shishkin OV, Pichugin KY, Gorb L, Leszczynski J (2002) J Mol Struct 616:159

    Article  CAS  Google Scholar 

  50. Zhigalko MV, Shishkin OV (2006) J Struct Chem 47:823

    Article  CAS  Google Scholar 

  51. Sheldrick G (2008) Acta Crystallogr Sect A 64:112

    Article  Google Scholar 

  52. Perrin DD, Armarego IF, Perrin DR (1980) Purification of laboratory chemicals, 2nd edn. Pergamon Press, New York

    Google Scholar 

Download references

Acknowledgments

Alexey Dobrydnev acknowledges Olga Nefedova for a fellowship. The authors also thank Prof. Olexander Turov for technical support.

Author information

Authors and Affiliations

  1. Chemistry Department, Kiev National Taras Shevchenko University, Vladimirskaya Street, 60, Kiev, 01033, Ukraine

    Alexey V. Dobrydnev, Tatyana A. Volovnenko & Yulian M. Volovenko

  2. Division of Functional Materials Chemistry, SSI “Institute for Single Crystals” National Academy of Science of Ukraine, Lenina Avenue, 60, Kharkiv, 61001, Ukraine

    Gennady V. Palamarchuk

  3. Department of Inorganic Chemistry, V.N. Karazin Kharkiv National University, Svobody Square, 4, Kharkiv, 61202, Ukraine

    Oleg V. Shishkin

Authors
  1. Alexey V. Dobrydnev
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Tatyana A. Volovnenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yulian M. Volovenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Gennady V. Palamarchuk
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Oleg V. Shishkin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Alexey V. Dobrydnev.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Dobrydnev, A.V., Volovnenko, T.A., Volovenko, Y.M. et al. Cyclic α-amino acids as precursors for synthesis of 2-amino-3-hetarylpyrrolin-4-ones and their spiro derivatives. Monatsh Chem 143, 779–789 (2012). https://doi.org/10.1007/s00706-012-0727-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-012-0727-3

Keywords

Search

Navigation