Skip to main content
SpringerLink
Log in

Stereoselective synthesis of homochiral paracyclophanylindenofuranylimidazo[3.3.3]propellanes

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

Abstract

The reaction between N-paracyclophanyl-substituted hydrazine-carbothioamides and dicyanomethylene-1,3-indanedione (CNIND) furnished planar and central chiral substituted (epiminomethanoimino)-indenofuranyl-1,4-(1,4-dibenzenocyclohexaphane)-1,2-carboxamides as a type of paracyclophanylfuroimidazo[3.3.3]propellanes in 35–81% yields as a major product as single diastereomers, and substituted spiro[indene-2,4′-indenopyran]-3′-carbonitrile (9–12% yields) as a minor product. To prepare the homochiral paracyclophanylpropellane, oxidation of scalemic formylparacyclophane afforded the corresponding acid. Afterward, the acid chloride formation of [2.2]paracyclophane was obtained by chlorination of the corresponding acid. By repeating the previous procedure and utilizing a final HPLC purification, we succeeded in obtaining the target homochiral propellane. Various spectroscopic techniques such as mass spectrometry, 1H NMR, 13C NMR, and X-ray analysis have been used for structure determination and confirmation of the stereochemistry of the isolated products.

Graphic 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

Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  1. Hassan Z, Spuling E, Knoll DM, Bräse S (2020) Angew Chem Int Ed 59:2156

    Article  CAS  Google Scholar 

  2. Hassan Z, Spuling E, Knoll DM, Lahann J, Bräse S (2018) Chem Soc Rev 47:6947

    Article  CAS  Google Scholar 

  3. Driggers EM, Hale SP, Lee J, Terrett NK (2008) Nat Rev Drug Discov 7:608

    Article  CAS  Google Scholar 

  4. Newman DJ, Cragg GM, Snader KM (2000) Nat Prod Rep 17:215

    Article  CAS  Google Scholar 

  5. Ridley D, Ritchie E, Taylor W (1970) Aust J Chem 23:147

    Article  CAS  Google Scholar 

  6. Aly AA, Hassan AA, AbdAl-Latif E-SS, Ibrahim MA, Bräse S, Nieger M (2018) Arkivoc iii:102

  7. Skultety M, Hübner H, Löber S, Gmeiner P (2010) J Med Chem 53:7219

    Article  CAS  Google Scholar 

  8. Löber S, Ortner B, Bettinetti L, Hübner H, Gmeiner P (2002) Tetrahedron Asymmetry 13:2303

    Article  Google Scholar 

  9. Ortner B, Waibel R, Gmeiner P (2001) Angew Chem Int Ed 40:1283

    Article  CAS  Google Scholar 

  10. Shingalapur RV, Hosamani KM, Keri RS, Hugar MH (2010) Eur J Med Chem 45:1753

    Article  CAS  Google Scholar 

  11. Kishore A, Nampurath GK, Mathew SP, Zachariah RT, Potu BK, Rao MS, Valiathan M, Chamallamudi MR (2009) Chem Biol Interact 177:242

    Article  CAS  Google Scholar 

  12. Aly AA, Brown AB, El-Emary TI, Mohamed AM, Mekheimer RAH (2009) Arkivoc i:150

  13. Cram DJ, Allinger NL (1955) J Am Chem Soc 77:6289

    Article  CAS  Google Scholar 

  14. Diederich FN (1991) Cyclophanes. Royal Society of Chemistry

    Google Scholar 

  15. Bolm C, Kuehn T (2000) Synlett 0899

  16. Knoll DM, Hu Y, Hassan Z, Nieger M, Bräse S (2019) Molecules 24:4122

    Article  Google Scholar 

  17. Knoll DM, Šimek H, Hassan Z, Bräse S (2019) Eur J Org Chem 6198

  18. Knoll DM, Wiesner TB, Marschner SM, Hassan Z, Weis P, Kappes M, Nieger M, Bräse S (2019) RSC Adv 9:30541

    Article  CAS  Google Scholar 

  19. Knoll DM, Zippel C, Hassan Z, Nieger M, Weis P, Kappes MM, Bräse S (2019) Dalton Trans 48:17704

    Article  CAS  Google Scholar 

  20. Gibson SE, Knight JD (2003) Org Biomol Chem 1:1256

    Article  CAS  Google Scholar 

  21. Banfi S, Manfredi A, Montanari F, Pozzi G, Quici S (1996) J Mol Catal A Chem 113:77

    Article  CAS  Google Scholar 

  22. Rozenberg V, Dubrovina N, Sergeeva E, Antonov D (1998) Tetrahedron Asymmetry 9:653

    Article  CAS  Google Scholar 

  23. Dilmac AM, Spuling E, de Meijere A, Bräse S (2017) Angew Chem Int Ed 56:5684

    Article  CAS  Google Scholar 

  24. Sugimoto Y, Babiker HA, Saisho T, Furumoto T, Inanaga S, Kato M (2001) J Org Chem 66:3299

    Article  CAS  Google Scholar 

  25. Tokuyama T, Daly J (1983) Tetrahedron 39:41

    Article  CAS  Google Scholar 

  26. Fieser L, Dunn J (1936) J Am Chem Soc 58:1054

    Article  CAS  Google Scholar 

  27. Fieser LF, Dunn J (1937) J Am Chem Soc 59:1021

    Article  CAS  Google Scholar 

  28. Brigl P, Herrmann R (1938) Ber Dtsch Chem Ges (A, B Ser) 71:2280

  29. Snatzke G, Zanati G (1965) Justus Liebigs Ann Chem 684:62

    Article  CAS  Google Scholar 

  30. Yavari I, Khajeh-Khezri A, Bahemmat S, Halvagar MR (2017) Synlett 28:1785

    Article  CAS  Google Scholar 

  31. Yavari I, Khajeh-Khezri A (2017) Mol Divers 21:849

    Article  CAS  Google Scholar 

  32. Hassan AA, Mohamed NK, Abd El-Haleem LE, Bräse S, Nieger M (2016) Curr Org Synth 13:426

    Article  CAS  Google Scholar 

  33. Hassan AA, Mohamed SK, Abdel-Latif FF, Mostafa SM, Abdel-Aziz M, Mague JT, Akkurt M (2016) Synlett 27:412

    Article  CAS  Google Scholar 

  34. Hassan AA, Mohamed NK, Aly AA, Tawfeek HN, Bräse S, Nieger M (2020) Mol Divers 1

  35. Hassan AA, Aly AA, Mohamed NK, El Shaieb KM, Makhlouf MM, Abdelhafez E-SM, Bräse S, Nieger M, Dalby KN, Kaoud TS (2019) Bioorg Chem 85:585

  36. Aly AA, Bräse S, Hassan AA, Mohamed NK, El-Haleem A, Lamiaa E, Nieger M, Morsy NM, Abdelhafez E (2020) Molecules 25:3089

    Article  CAS  Google Scholar 

  37. Gewald K, Schindler R (1990) J Prakt Chem 332:223

    Article  CAS  Google Scholar 

  38. Radeglia R (1985) J Prakt Chem 327:878

    Article  Google Scholar 

  39. Kundu A, Pramanik A (2015) Mol Divers 19:459

    Article  CAS  Google Scholar 

  40. Braun C, Bräse S, Schafer LL (2017) Eur J Org Chem 1760

  41. Hopf H, Narayanan SV, Jones PG (2015) Beilstein J Org Chem 11:437

    Article  CAS  Google Scholar 

  42. Zitt H, Dix I, Hopf H, Jones PG (2002) Eur J Org Chem 2298

  43. Aly AA, Bräse S, Hassan AA, Mohamed NK, El-Haleem LEA, Nieger M (2020) Molecules 25:3315

    Article  CAS  Google Scholar 

  44. Sheldrick GM (2015) Acta Crystallogr A 71:3

    Article  Google Scholar 

  45. Sheldrick GM (2015) Acta Crystallogr C 71:3

    Article  Google Scholar 

  46. Spek AL (2009) Acta Crystallogr D 65:148

    Article  CAS  Google Scholar 

  47. Spek AL (2015) Acta Crystallogr C 71:9

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors thank Egyptian Mission, Ministry of Higher Education, Egypt for their financial support to Mrs. Lamiaa E. Abd El-Haleem during her accommodation in Karlsruhe Institute für Technology, Karlsruhe, Germany.

Author information

Authors and Affiliations

  1. Chemistry Department, Faculty of Science, Minia University, El-Minia, 61519, Egypt

    Alaa A. Hassan, Ashraf A. Aly, Nasr K. Mohamed & Lamiaa E. Abd El-Haleem

  2. Institute of Organic Chemistry, Karlsruhe Institute of Technology, Fritz-Haber-Weg 6, 76131, Karlsruhe, Germany

    Stefan Bräse & Lamiaa E. Abd El-Haleem

  3. Institute of Biological and Chemical Systems-Functional Molecular Systems (IBCS-FMS), Karlsruhe Institute of Technology, Hermann-von-Helmholtz-Platz 1, 76344, Eggenstein-Leopoldshafen, Germany

    Stefan Bräse

  4. Department of Chemistry, University of Helsinki, A. I. Virtasen aukio I, P.O. Box 55, 00014, Helsinki, Finland

    Martin Nieger

Authors
  1. Alaa A. Hassan
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Stefan Bräse
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Ashraf A. Aly
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Nasr K. Mohamed
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Lamiaa E. Abd El-Haleem
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Martin Nieger
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Alaa A. Hassan or Stefan Bräse.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary Information

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Hassan, A.A., Bräse, S., Aly, A.A. et al. Stereoselective synthesis of homochiral paracyclophanylindenofuranylimidazo[3.3.3]propellanes. Monatsh Chem 152, 1571–1579 (2021). https://doi.org/10.1007/s00706-021-02853-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-021-02853-0

Keywords

Search

Navigation