Skip to main content
SpringerLink
Log in

Syntheses and Crystal Structures of Three Electron Poor N-Vinyltheophylline Derivatives

  • Original Paper
  • Published:
Journal of Chemical Crystallography Aims and scope Submit manuscript

Abstract

Protonation of the highly reactive 1:1 intermediates, produced in the reaction between triphenylphosphine and alkyl acetylenecarboxylates (or dialkyl acetylenedicarboxylates) by theophylline leads to vinyltriphenylphosphonium salts, which undergo Michael addition reaction with conjugate base to produce phosphorus ylides. Silica gel was found to catalyze conversion of the phosphorus ylides to electron-poor N-vinyl imidazoles in solvent-free conditions under thermal (90 °C, 1 h) conditions. The structures of these compounds were confirmed by IR, 1H, and 13C NMR spectroscopy, and single crystal X-ray structure determination. The structural analysis of the products indicated that the reaction is completely regio- and stereoselective.

Graphical Abstract

The syntheses of titled compounds were achieved in one pot using alkyl acetylenecarboxylates (or dialkyl acetylenedicarboxylates), triphenylphosphine and theophylline in the presence of a catalytic amount of silica gel. The structures of these compounds were confirmed by IR, 1H, and 13C NMR spectroscopy, and single crystal X-ray structure determination. X-ray crystal studies were undertaken for three compounds and the results are presented. The structural analysis of the products indicated that the reaction is completely regio- and stereoselective.

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
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5

Similar content being viewed by others

References

  1. Kamaraj K, Kim E, Galliker B, Zakharov NL, Rheingold RA, Zuberbuhler DA, Karlin DK (2003) J Am Chem Soc 15:6028–6029

    Article  Google Scholar 

  2. Moore RL, Cooks MS, Anderson SM, Schanz JH, Griffin TS, Rogers DR, Kirk CM, Shaughnessy KH (2006) Organometallics 25:5151–5158

    Article  CAS  Google Scholar 

  3. Wiglenda T, Gust R (2007) J Med Chem 50:1475–1484

    Article  CAS  Google Scholar 

  4. Baran SP, O’Malley PD, Zografos LA (2004) Angew Chem Int Ed 43:2674–2677

    Article  CAS  Google Scholar 

  5. O’Malley PD, Li K, Maue M, Zografos LA, Baran SP (2007) J Am Chem Soc 129:4762–4775

    Article  Google Scholar 

  6. Wang R, Xiao CJ, Twamley B, Shreeve MJ (2007) Org Biomol Chem 5:671–678

    Article  CAS  Google Scholar 

  7. Kan CH, Tseng CM, Chu HY (2007) Tetrahedron 63:1644–1653

    Article  CAS  Google Scholar 

  8. Lantz WL, Manasia JP (1970) Shell Oil Co. US 3,538,039

  9. Kolodiazhnyi OI (1999) Phosphorus ylides: chemistry and applications in organic chemistry. Wiley, New York

    Google Scholar 

  10. Kaska WC (1983) Coord Chem Rev 48:1–58

    Article  CAS  Google Scholar 

  11. Maryanoff BE, Reitz AB (1989) Chem Rev 89:863–927

    Article  CAS  Google Scholar 

  12. Cobridge DEC (1995) Phosphorus: an outline of chemistry, biochemistry and uses, 5th edn. Elsevier, Amsterdam

    Google Scholar 

  13. Yavari I, Ramazani A (1996) Synth Commun 26:4495–4499

    Article  CAS  Google Scholar 

  14. Yavari I, Ramazani A (1997) Phosphorus Sulfur Silicon 130:73–77

    Article  CAS  Google Scholar 

  15. Ramazani A, Bodaghi A (2000) Tetrahedron Lett 41:567–568

    Article  CAS  Google Scholar 

  16. Ramazani A, Kazemizadeh AR, Ahmadi E, Ślepokura K, Lis T (2006) Z Naturforsch 61b:1128–1133

    Google Scholar 

  17. Souldozi A, Ramazani A, Bouslimani N, Welter R (2007) Tetrahedron Lett 48:2617–2620

    Article  CAS  Google Scholar 

  18. Souldozi A, Ramazani A (2007) Tetrahedron Lett 48:1549–1551

    Article  CAS  Google Scholar 

  19. Pakravan P, Ramazani A, Noshiranzadeh N, Sedrpoushan A (2007) Phosphorus Sulfur Silicon 182:545–549

    Article  CAS  Google Scholar 

  20. Ramazani A, Rahimifard M, Souldozi A (2007) Phosphorus Sulfur Silicon 182:1–5

    Article  CAS  Google Scholar 

  21. Tofangchi Mahyari A, Shajari N, Kazemizadeh AR, Ślepokura K, Lis T, Ramazani A (2007) Z Naturforsch 62b:829–834

    Google Scholar 

  22. Ramazani A, Rahimifard M, Noshiranzadeh N, Souldozi A (2007) Phosphorus Sulfur Silicon 182:413–417

    Article  CAS  Google Scholar 

  23. Ramazani A, Rezaei A (2010) Org Lett 12:2852

    Article  CAS  Google Scholar 

  24. Ramazani A, Kazemizadeh AR, Ahmadi E, Noshiranzadeh N, Souldozi A (2008) Curr Org Chem 12:59

    Article  CAS  Google Scholar 

  25. Allen FH (2002) Acta Crystallogr B 58:380; see for example CSD refcodes: EDOSUM, YINGAE, KITNIL, KITNOR

  26. KUMA KM4CCD software: CrysAlis CCD and CrysAlis RED, Version 1.171. Oxford Diffraction Ltd. (2003) p 7

  27. Sheldrick GM (2008) Acta Crystallogr A 64:112

    Article  Google Scholar 

  28. XP-interactive molecular graphics, version 5.1. Bruker Analytical X-Ray Systems (1998)

Download references

Author information

Authors and Affiliations

  1. Chemistry Department, Zanjan University, PO Box 45195-313, Zanjan, Iran

    Ali Ramazani, Azam Farshadi & Amir Mahyari

  2. Faculty of Chemistry, University of Wrocław, 14 Joliot-Curie Street, 50-383, Wrocław, Poland

    Katarzyna Ślepokura & Tadeusz Lis

  3. Young Researchers Club, Zanjan Branch, Islamic Azad University, Zanjan, Iran

    Morteza Rouhani

Authors
  1. Ali Ramazani
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Azam Farshadi
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Amir Mahyari
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Katarzyna Ślepokura
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Tadeusz Lis
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Morteza Rouhani
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ali Ramazani.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Ramazani, A., Farshadi, A., Mahyari, A. et al. Syntheses and Crystal Structures of Three Electron Poor N-Vinyltheophylline Derivatives. J Chem Crystallogr 41, 1376–1385 (2011). https://doi.org/10.1007/s10870-011-0107-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10870-011-0107-6

Keywords

Search

Navigation