Skip to main content
Log in

Synthesis of spiro 2-(5-amino-2,3-dihydro-3-oxopyrrol-4-yl)-1,3-dialkylbenzimidazolium chlorides

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

Abstract

The interaction of 1,3-dialkyl-2,3-dihydro-1H-benzo[d]imidazol-2-ylidenemethyl cyanides 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-(5-amino-2,3-dihydro-3-oxopyrrol-4-yl)-1,3-dialkylbenzimidazolium chlorides.

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
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. Dubinina HH, Volovenko YuM (2007) Compound of 1,4-disubstituted 5-amino-1,2-dihydropyrol-3-on, having anticarcinogenic activity. Ukrainian Pat UA22204

  2. Volovenko YM, Tverdokhlebov AV, Gorulya AP, Shishkina SV, Zubatyuk RI, Shishkin OV (2002) Eur J Org Chem 4:663

    Article  Google Scholar 

  3. Tverdokhlebov AV, Volovenko YM, Shokol TV (1998) Chem Heterocycl Compd 34:44

    Article  CAS  Google Scholar 

  4. Resnyanskaya EV, Shokol TV, Volovenko YM, Tverdokhlebov AV (1999) Chem Heterocycl Compd 35:1230

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  6. Tverdokhlebov AV, Lyashenko AB, Volovenko YM, Tolmachev AA (2004) Chem Heterocycl Compd 40:1536

    Article  CAS  Google Scholar 

  7. Tverdokhlebov AV, Denisenko AV, Tolmachev AA, Volovenko YM (2007) Synthesis 1811

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  13. Dobrydnev AV, Volovnenko TA, Volovenko YM, Palamarchuk GV, Shishkin OV (2012) Monatsh Chem 143:779

    Article  CAS  Google Scholar 

  14. Dobridnev AV, Volovnenko TA, Turov AV, Volovenko YM (2010) Chem Heterocycl Compd 46:887

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  17. Shishkin OV, Konovalova IS, Zubatyuk RI, Palamarchuk GV, Shishkina SV, Biitseva AV, Rudenko IV, Tkachuk VA, Kornilov MY, Hordiyenko OV, Leszczynski J (2013) Struct Chem 24:1089

    Article  CAS  Google Scholar 

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

    Google Scholar 

  19. Sheldrick G (2008) Acta Cryst Sect A 64:112

    Article  CAS  Google Scholar 

  20. Zhao Y, Truhlar DG (2008) Acc Chem Res 41:157

    Article  CAS  Google Scholar 

  21. Foster JP, Weinhold F (1980) J Am Chem Soc 24:7211

    Article  Google Scholar 

  22. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA Jr, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas Ö, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2009) Gaussian09, Rev A.1. Gaussian Inc, Wallingford

    Google Scholar 

Download references

Acknowledgments

Alexey Dobrydnev acknowledges Patricia Dobrydneva for a fellowship and technical support.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Alexey V. Dobrydnev.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Dobrydnev, A.V., Volovenko, Y.M., Turov, A.V. et al. Synthesis of spiro 2-(5-amino-2,3-dihydro-3-oxopyrrol-4-yl)-1,3-dialkylbenzimidazolium chlorides. Monatsh Chem 146, 931–939 (2015). https://doi.org/10.1007/s00706-015-1438-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-015-1438-3

Keywords

Navigation