Skip to main content
SpringerLink
Log in

Friedel–Crafts chemistry 56*. Unprecedented construction of functionalized polycyclic quinolines via Friedel–Crafts cycliacylation and Beckmann rearrangement

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Construction of functionalized tetracyclic pyrazolo-fused cyclohepta[2,3-h]-, azepino[4,5-h]-, azocino[5,4-h]-, azocino[4,5-h]-, azonino[5,6-h]-, and azocino[2,3-h]quinolinones has been demonstrated by performing intramolecular Friedel–Crafts acylation and Beckmann rearrangement. Trifluoromethanesulfonic or polyphosphoric acid-assisted cyclization of N-heterocyclic acids and esters, synthesized from 1-phenyl-3-(quinolin-8-yl)-1H-pyrazole-4-carbaldehyde, allows to obtain tetracyclic ketones. Further polyphosphoric acid-mediated Beckmann rearrangement of cyclohepta[1,2-h]quinolinone oximes provides the respective lactams in high yields.

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

Figure 1.
Figure 2.

Similar content being viewed by others

References

  1. Khalaf, A. A.; Abd El-Aal, H. A. K. Assiut Univ. J. Chem. 2018, 47, 66.

    Google Scholar 

  2. (a) Michael, J. P. Nat. Prod. Rep. 2008, 25, 166. (b) Wagman, A. S.; Wentland, M. P. In Comprehensive Medicinal Chemistry II; Taylor, J. B.; Triggle, D. J., Eds.; Elsevier: Oxford, 2007, Vol. 7, p. 567. (c) Xu, X.; Yang, Y.; Zhang, X.; Yi, W. Org. Lett. 2018, 20, 566. (d) Chung, P.-Y.; Bian, Z.-X.; Pun, H.-Y.; Chan, D.; Chan, A. S.-C.; Chui, C.-H.; Tang, J. C.-O.; Lam, K.-H. Future Med. Chem. 2015, 7, 947. (e) Wiesner, J.; Ortmann, R.; Jomaa, H.; Schlitzer, M. Angew. Chem., Int. Ed. 2003, 42, 5274. (f) Kaur, K.; Jain, M.; Reddy, R. P.; Jain, R. Eur. J. Med. Chem. 2010, 45, 3245. (g) Zhu, L.; Qiu, R.; Cao, X.; Xiao, S.; Xu, X.; Au, C.-T.; Yin, S.-F. Org. Lett. 2015, 17, 5528. (h) Lee, S. Y.; Jeon, J.; Cheon, C.-H. J. Org. Chem. 2018, 83, 5177. (i) Kouznetsov, V. V.; Romero Bohórquez, A. R.; Astudillo Saavedra, L. Synthesis 2009, 4219. (j) Martínková, L.; Křen, V.; Cvak, L.; Ovesná, M.; Přepechalová, I. J. Biotechnol. 2000, 84, 63. (k) Schiff, P. L. Am. J. Pharm. Educ. 2006, 70, 98. (l) Vree, T. B.; van Dongen, R. T. M.; Koopman-Kimenai, P. M. Int. J. Clin. Pract. 2000, 54, 395. (m) Gardiner, S. J.; Begg, E. J. Pharmacol. Rev. 2006, 58, 521. (n) Ma, F.; Zhang, J.; Zhang, J.; Zhang, C. Cell. Mol. Immunol. 2010, 7, 381. (o) Buitendijk, M.; Eszterhas, S. K.; Howell, A. L. AIDS Res. Hum. Retrovir. 2013, 29, 907. (p) Morteza-Semnani, K; Amin, Gh.; Shidfar, M. R.; Hadizadeh, H.; Shafiee, A. Fitoterapia 2003, 74, 493. (q) Asencio, M; Hurtado-Guzmán, C; López, J. J.; Cassels, B. K.; Protais, P.; Chagraoui, A. Bioorg. Med. Chem. 2005, 13, 3699. (r) Imbimbo, B. P.; Broccali, G.; Cesana, M.; Crema, F.; Attardo-Parrinello, G. Antimicrob. Agents Chemother. 1991, 35, 390. (s) Ehrlich, P. P.; Ralston, J. W.; Michaelides, M. R. J. Org. Chem. 1997, 62, 2782. (t) Gorelick, D. A.; Gardner, E. L.; Xi, Z.-X. Drugs 2004, 64, 1547. (u) Zhang, J.; Xiong, B.; Zhen, X.; Zhang, A. Med. Res. Rev. 2009, 29, 272. (v) Dewick, P. M. Medicinal Natural Products: A Biosynthetic Approach; John Wiley & Sons: Chichester, 2002, 2nd ed., p. 315.

  3. Fotie, J.; Kemami Wangun, H. V.; Fronczek, F. R.; Massawe, N.; Bhattarai, B. T.; Rhodus, J. L.; Singleton, T. A.; Bohle, D. S. J. Org. Chem. 2012, 77, 2784.

    Article  CAS  PubMed  Google Scholar 

  4. Varala, R.; Enugala, R.; Adapa, S. R. Synthesis 2006, 3825.

  5. Ramann, G. A.; Cowen, B. J. Tetrahedron Lett. 2015, 56, 6436.

    Article  CAS  Google Scholar 

  6. Li, J. J. Name Reactions: A Collection of Detailed Mechanisms and Synthetic Applications; Springer-Verlag: Heidelberg, 2009, p. 131.

    Book  Google Scholar 

  7. Gao, Q.; Liu, S.; Wu, X.; Zhang, J.; Wu, A. J. Org. Chem. 2015, 80, 5984.

    Article  CAS  PubMed  Google Scholar 

  8. (a) Saunthwal, R. K.; Patel, M.; Verma, A. K. J. Org. Chem. 2016, 81, 6563. (b) Babu, G.; Perumal, P. T. Tetrahedron Lett. 1998, 39, 3225.

  9. Upadhayaya, R. S.; Lahore, S. V.; Sayyed, A. Y.; Dixit, S. S.; Shinde, P. D.; Chattopadhyaya, J. Org. Biomol. Chem. 2010, 8, 2180.

    Article  CAS  PubMed  Google Scholar 

  10. Shvekhgeimer, M. G.-A. Chem. Heterocycl. Compd. 2004, 40, 257. [Khim. Geterotsikl. Soedin. 2004, 323.]

  11. Gattu, R.; Basha, R. S.; Bagdi, P. R.; Khan, A. T. RSC Adv. 2016, 6, 11675.

    Article  CAS  Google Scholar 

  12. Qu, F.; He, P.; Hu, R.-F.; Cheng, X.-H.; Wang, S.; Wu, J. Synth. Commun. 2015, 45, 2802.

    Article  CAS  Google Scholar 

  13. Baumann, M.; Baxendale, I. R. J. Org. Chem. 2015, 80, 10806.

    Article  CAS  PubMed  Google Scholar 

  14. Yang, Y.-Y.; Shou, W.-G.; Chen, Z.-B.; Hong, D.; Wang, Y.-G. J. Org. Chem. 2008, 73, 3928.

    Article  CAS  PubMed  Google Scholar 

  15. Willumstad, T. P.; Boudreau, P. D.; Danheiser, R. L. J. Org. Chem. 2015, 80, 11794.

    Article  CAS  PubMed  Google Scholar 

  16. (a) Kang, Y. K.; Kim, D. Y. Chem. Commun. 2014, 50, 222. (b) Suh, C. W.; Kim, D. Y. Org. Lett. 2014, 16, 5374. (c) Suh, C. W.; Woo, S. B.; Kim, D. Y. Asian J. Org. Chem. 2014, 3, 399.

  17. (a) Luo, C.-Z.; Gandeepan, P.; Wu, Y.-C.; Chen, W.-C.; Cheng, C.-H. RSC Adv. 2015, 5, 106012. (b) Li, X.; Mao, Z.; Wang, Y.; Chen, W.; Lin, X. Tetrahedron 2011, 67, 3858.

  18. (a) Yella, R.; Gottlieb, H. E.; Hoz, S. J. Org. Chem. 2015, 80, 8929. (b) Kim, Y. J.; Kim, Y.; Kim, D. Y. Bull. Korean Chem. Soc. 2017, 38, 578. (c) Kang, Y. K.; Kim, S. M.; Kim, D. Y. J. Am. Chem. Soc. 2010, 132, 11847.

  19. (a) Groeper, J. A.; Liao, X.; Lu, Z. US Patent 10131660, 2018. (b) Ghoshal, A.; Yugandhar, D.; Nanubolu, J. B.; Srivastava, A. K. ACS Comb. Sci. 2017, 19, 600. (c) Shutske, G. M.; Kapples, K. J. US Patent 6248750, 2001. (d) Galli, A.; Ranaudo, E.; Giannini, L.; Costagli, C. J. Pharm. Pharmacol. 1996, 48, 1164. (e) Acosta Quintero, L. M.; Burgos, I.; Palma, A.; Cobo, J.; Glidewell, C. Acta Crystallogr., Sect. C: Struct. Chem. 2016, C72, 52. (f) Prunier, H.; Rault, S.; Lancelot, J.-C.; Robba, M.; Renard, P.; Delagrange, P.; Pfeiffer, B.; Caignard, D.-H.; Misslin, R.; Guardiola-Lemaitre, B.; Hamon, M. J. Med. Chem. 1997, 40, 1808. (g) Singh, V.; Hutait, S.; Batra, S. Eur. J. Org. Chem. 2009, 3454. (h) Shutske, G. M.; Effland, R. C. EP Patent 287977, 1994.

  20. Di Pietro, O; Vicente-García, E; Taylor, M. C.; Berenguer, D.; Viayna, E.; Lanzoni, A.; Sola, I.; Sayago, H.; Riera, C.; Fisa, R.; Victòria Clos, M.; Pérez, B.; Kelly, J. M.; Lavilla, R.; Muñoz-Torrero, D. Eur. J. Med. Chem. 2015, 105, 120.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  21. Konda, S. R.; Reguri, B. R.; Kagga, M. Der Pharma Chem. 2014, 6, 250.

    Google Scholar 

  22. Zhidkova, A. M.; Granik, V. G.; Glushkov, R. G.; Vlasova, T. F.; Anisimova, O. S.; Gus'kova, T. A.; Pershin, G. N. Chem. Heterocycl. Compd. 1974, 10, 579. [Khim. Geterotsikl. Soedin. 1974, 670.]

  23. Kuroki, Y.; Fujiwara, H.; Nishino, S.; Nakamura, I.; Tokunaga, H. EP Patent 0430485, 1991.

  24. Cappelli, A.; Anzini, M.; Vomero, S. Heterocycles 1994, 38, 1265.

    Article  CAS  Google Scholar 

  25. Hinschberger, A.; Butt, S.; Lelong, V.; Boulouard, M.; Dumuis, A.; Dauphin, F.; Bureau, R.; Pfeiffer, B.; Renard, P.; Rault, S. J. Med. Chem. 2003, 46, 138.

    Article  CAS  PubMed  Google Scholar 

  26. Lavielle, G.; Cimetiere, B.; Verbeuren, T.; Simonet, S.; Descombes, J.-J. EP Patent 1118610, 2001.

  27. (a) Simpson, J. C. E.; Atkinson, C. M.; Schofield, K.; Stephenson, O. J. Chem. Soc. 1945, 646. (b) Yokoo, A.; Morosawa, S. Bull. Chem. Soc. Jpn. 1956, 29, 631. (c) Abd El-Aal, H. A. K. Aust. J. Chem. 2017, 70, 1082. (d) Baruah, B.; Bhuyan, P. J. Tetrahedron 2009, 65, 7099. (e) Neuschl, M.; Bogdal, D.; Potacek, M. Molecules 2007, 12, 49.

  28. (a) Kubo, A.; Saito, N.; Yamato, H.; Masubuchi, K.; Nakamura, M. J. Org. Chem. 1988, 53, 4295. (b) Takayama, Y.; Yamada, T.; Tatekabe, S.; Nagasawa, K. Chem. Commun. 2013, 49, 6519. (c) Yadav, J. S.; Gayathri, K. U.; Subba Redy, B. V.; Prasad, A. R. Synlett 2009, 43. (d) Chen, Y.; Yekta, S.; Yudin, A. K. Chem. Rev. 2003, 103, 3155. (e) Muratake, H.; Natsume, M. Heterocycles 1990, 31, 683. (f) Wales, S. M.; Walker, M. M.; Johnson, J. S. Org. Lett. 2013, 15, 2558. (g) Huffman, J. W.; Smith, V. J.; Padgett, L. W. Tetrahedron 2008, 64, 2104. (h) Shingare, R. D.; Velayudham, R.; Gawade, J. R.; Reddy, D. S. Org. Lett. 2013, 15, 4556. (i) Matsuzawa, H.; Miyake, Y.; Nishibayashi, Y. Angew. Chem., Int. Ed. 2007, 46, 6488. (j) Jørgensen, K. A. Synthesis 2003, 1117. (k) Carmona, O.; Greenhouse, R.; Landeros, R.; Muchowski, J. M. J. Org. Chem. 1980, 45, 5336. (l) Ottoni, O.; de V. F. Neder, A.; Dias, A. K. B.; Cruz, R. P. A.; Aquino, L. B. Org. Lett. 2001, 3, 1005. (m) Shirai, A.; Miyata, O.; Tohnai, N.; Miyata, M.; Procter, D. J.; Sucunza, D.; Naito, T. J. Org. Chem. 2008, 73, 4464. (n) Zhao, Y.-L.; Lou, Q.-X.; Wang, L.-S.; Hu, W.-H.; Zhao, J.-L. Angew. Chem., Int. Ed. 2017, 56, 338. (o) Buckingham, J.; Baggaley, K. H.; Roberts, A. D.; Szabó, L. F. Dictionary of Alkaloids; CRC Press: Boca Raton, 2010, 2nd ed.

  29. (a) Olah, G. A. Friedel–Crafts Chemistry; Wiley: New York, 1973. (b) Barclay, L. R. C. In Friedel–Crafts and Related Reactions; Olah, G. A., Ed.; Interscience Publishers: New York, 1964, vol. 2, p. 785. (c) Roberts, R. M.; Khalaf, A. A. Friedel–Crafts Alkylation Chemistry: A Century of Discovery; Marcel Dekker: New York, 1984. (d) Poulsen, T. B.; Jørgensen, K. A. Chem. Rev. 2008, 108, 2903.

  30. (a) Khalaf, A. A.; Roberts, R. M. J. Org. Chem. 1969, 34, 3571. (b) Khalaf, A. A.; Roberts, R. M. J. Org. Chem. 1966, 31, 89. (c) Khalaf, A. A.; Roberts, R. M. J. Org. Chem. 1972, 37, 4227. (d) Khalaf, A. A.; Albar, H. A. J. Indian Chem. Soc. 2004, 81, 518. (e) Khalaf, A. A.; Awad, I. M.; El-Emary, T. I.; Abd El-Aal, H. A. K. J. Indian Chem. Soc. 2006, 83, 1018. (f) Khalaf, A. A.; Roberts, R. M. J. Org. Chem. 1973, 38, 1388.

  31. (a) Abd El-Aal, H. A. K.; Khalaf, A. A. Aust. J. Chem. 2019, 72, 276. (b) Abd El-Aal, H. A. K. ARKIVOC 2018, (iii), 45. (c) Abd El-Aal, H. A. K.; Khalaf, A. A. J. Serb. Chem. Soc. 2013, 78, 611. (d) Abd El-Aal, H. A. K.; Khalaf, A. A.; El-Khawaga, A. M. A. J. Heterocycl. Chem. 2014, 51, 262.

  32. Campbell, K. N.; Kerwin, J. F.; LaForge, R. A.; Campbell, B. K. J. Am. Chem. Soc. 1946, 68, 1844.

    Article  CAS  PubMed  Google Scholar 

  33. Mikhaleva, A. I.; Ivanov, A. V.; Skital'tseva, E. V.; Ushakov, I. A.; Vasil'tsov, A. M.; Trofimov, B. A. Synthesis 2009, 587.

  34. Rokade, B. V.; Prabhu, K. R. J. Org. Chem. 2012, 77, 5364.

    Article  CAS  PubMed  Google Scholar 

  35. Taylor, R. J. Electrophilic Aromatic Substitution; Wiley: New York, 1990, p. 222.

    Google Scholar 

  36. (a) Olah, G. A.; Krishnamurti, R.; Surya Prakash, G. K. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, Vol. 3, p. 293. (b) Abd El-Aal, H. A. K.; Khalaf, A. A. Polycycl. Aromat. Compd. 2013, 33, 331. (c) Khalaf, A. A.; El-Khawaga, A. M.; Awad, I. M.; Abd El-Aal, H. A. K. ARKIVOC 2009, (xiv), 314. (d) Klumpp, D. A.; Rendy, R.; Zhang, Y.; McElrea, A.; Gomez, A.; Dang, H. J. Org. Chem. 2004, 69, 8108.

  37. (a) Yokoyama, N.; Arai, T. Chem. Commun. 2009, 3285. (b) Elkaeed, E. B.; An, J.; Beauchemin, A. M. J. Org. Chem. 2017, 82, 9890. (c) Kim, H. Y.; Song, E.; Oh, K. Org. Lett. 2017, 19, 312. (d) Chen, L.; Zhou, F.; Shi, T.-D.; Zhou, J. J. Org. Chem. 2012, 77, 4354. (e) Milstein, N. J. Heterocycl. Chem. 1968, 5, 339. (f) Wang, Y.-Q.; Song, J.; Hong, R.; Li, H.; Deng, L. J. Am. Chem. Soc. 2006, 128, 8156. (g) Kurkovskaya, L. N.; Khoshtariya, T. E. Chem. Heterocycl. Compd. 1995, 31, 938. [Khim. Geterotsikl. Soedin. 1995, 1078.]

  38. (a) Galli, C.; Mandolini, L. Eur. J. Org. Chem. 2000, 3117. (b) Kirkland, T. A.; Grubbs, R. H. J. Org. Chem. 1997, 62, 7310.

  39. Silverstein, R. M.; Webster, F. X.; Kiemle, D. J. Spectrometric Identification of Organic Compounds; Wiley: Hoboken, 2005.

    Google Scholar 

Download references

The authors gratefully acknowledge Department of Chemistry, Faculty of Science, Assiut University for providing all the necessary facilities.

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Assiut University, Assiut, 71516, Egypt

    Hassan A. K. Abd El-Aal & Ali A. Khalaf

Authors
  1. Hassan A. K. Abd El-Aal
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ali A. Khalaf
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Hassan A. K. Abd El-Aal.

Additional information

Supplementary information file containing 1H and 13C NMR spectra as well as data of elemental analyses of the synthesized compounds is available at the journal website at http://link.springer.com/journal/10593.

* For Communication 55, see1.

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(7), 632–643

Electronic supplementary material

ESM 1

(PDF 7757 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Abd El-Aal, H.A.K., Khalaf, A.A. Friedel–Crafts chemistry 56*. Unprecedented construction of functionalized polycyclic quinolines via Friedel–Crafts cycliacylation and Beckmann rearrangement. Chem Heterocycl Comp 55, 632–643 (2019). https://doi.org/10.1007/s10593-019-02509-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-019-02509-2

Keywords

Search

Navigation