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RESEARCH ARTICLE
Contents Vol 72(12)

Synthesis of Tetracyclic Fused Quinolines via a Friedel–Crafts and Beckmann Ring Expansion Sequence

Hassan A. K. Abd El-Aal A B and Talaat I. El-Emary A
+ Author Affiliations
- Author Affiliations

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

B Corresponding author. Email: hassankotb@aun.edu.eg

Australian Journal of Chemistry 72(12) 945-956 https://doi.org/10.1071/CH19363
Submitted: 5 August 2019  Accepted: 12 September 2019   Published: 6 November 2019

Abstract

An efficient protocol for the construction of tetracyclic fused quinolines (pyrazole-fused azepino-, azocino-, and azonino[3,2-b]quinolinones) via consecutive Friedel–Crafts and Beckmann reactions has been developed. The key steps in the syntheses of these new molecular scaffolds involve acid-mediated cyclization of 2-(pyrazol-3-yl)quinoline based carboxylic acids 6a–c, 8, and 12 to ketones 13a–e, followed by Beckmann rearrangements of the corresponding oximes 14a–e to provide the tetracyclic-fused quinoline skeletons 15a–e. Structures of synthesised compounds without stereochemical implication were confirmed by NMR and elemental analyses.


References

[1]  (a) V. V. Kouznetsov, B. A. R. Romero, L. A. Saavedra, Synthesis 2009, 4219.
      (b) V. F. Batista, D. C. G. A. Pinto, A. M. S. Silva, ACS Sustain. Chem. & Eng. 2016, 4, 4064.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) F. Ma, J. Zhang, J. Zhang, C. Zhang, Cell. Mol. Immunol. 2010, 7, 381.
         | Crossref | GoogleScholarGoogle Scholar |
         (d) A. S. Wagman, M. P. Wentland, in Comprehensive Medicinal Chemistry II (Eds J. B. Taylor, D. J. Triggle) 2007, Vol. 7, pp. 567–596 (Elsevier: Oxford).
      (e) M. Buitendijk, S. K. Eszterhas, A. L. Howell, AIDS Res. Hum. Retroviruses 2013, 29, 907.
         | Crossref | GoogleScholarGoogle Scholar |
         (f) See p. 315 in: P. M. Dewick, Medicinal Natural Products: A Biosynthetic Approach (2nd edn) 2002 (John Wiley & Sons: Chichester).
      (g) L. Zhu, R. Qiu, X. Cao, S. Xiao, X. Xu, C.-T. Au, S.-F. Yin, Org. Lett. 2015, 17, 5528.
         | Crossref | GoogleScholarGoogle Scholar |
      (h) X. Xu, Y. Yang, X. Zhang, W. Yi, Org. Lett. 2018, 20, 566.
         | Crossref | GoogleScholarGoogle Scholar |
      (i) S. J. Gardiner, E. J. Begg, Pharmacol. Rev. 2006, 58, 521.
         | Crossref | GoogleScholarGoogle Scholar |

[2]  (a) P. Y. Chung, Z. X. Bian, H. Y. Pun, D. Chan, A. S. Chan, C. H. Chui, J. C. Tang, K. H. Lam, Future Med. Chem. 2015, 7, 947.
         | Crossref | GoogleScholarGoogle Scholar | 26061110PubMed |
      (b) L. Martínková, V. Kren, L. Cvak, M. Ovesná, I. Prepechalová, J. Biotechnol. 2000, 84, 63.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) S. Inuki, A. Iwata, S. Oishi, N. Fujii, H. Ohno, J. Org. Chem. 2011, 76, 2072.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) Y. Pommier, C. Redon, V. A. Rao, J. A. Seiler, O. Sordet, H. Takemura, S. Antony, L. Meng, Z. Liao, G. Kohlhagen, Mutat. Res. 2003, 532, 173.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) M. Mizuta, H. Kanamori, J. Chem. Soc. 1957, 2177.
         (f) C. Geoffrey (Ed.), The Alkaloids: Chemistry and Biology 2003, pp. 1–50 (Academic Press: New York, NY).

[3]     (a) K. R. Alper, S. D. Glick, in The Alkaloids (Ed. G. A. Cordell) 2001, Vol. 56, pp. 1–38 (Academic Press: New York, NY).
      (b) C. E. Nge, W. C. Kam, N. F. Thomas, S.-H. Lim, Y.-Y. Low, T.-S. Kam, J. Nat. Prod. 2016, 79, 1388.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) A. C. Kruegel, S. Rakshit, X. Li, D. Sames, J. Org. Chem. 2015, 80, 2062.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) Y. Zhang, L. Guo, G. Yang, F. Guo, Y. Di, S. Li, D. Chen, X. Hao, Fitoterapia 2015, 100, 150.
         | Crossref | GoogleScholarGoogle Scholar |

[4]     (a) G. Haufe, G. Mann, Chemistry of Alicyclic Compounds 1989 (Elsevier: Amsterdam).
         (b) M. Grossel, Alicyclic Chemistry 1997 (Oxford University Press: New York, NY).

[5]     (a) M. Hanack, Conformational Theory 1965 (Academic Press: New York, NY).
         (b) E. L. Eliel, S. H. Wilen, Stereochemistry of Organic Compounds 1994 (Wiley: New York, NY).

[6]  Q. Guo, W. Wang, W. Teng, L. Chen, Y. Wang, B. Shen, Synth. Commun. 2012, 42, 2574.
         | Crossref | GoogleScholarGoogle Scholar |

[7]  M. Shvekhgeimer, Chem. Heterocycl. Compd. 2004, 40, 257.
         | Crossref | GoogleScholarGoogle Scholar |

[8]  J.-C. Brouet, S. Gu, N. P. Peet, J. D. Williams, Synth. Commun. 2009, 39, 1563.
         | Crossref | GoogleScholarGoogle Scholar |

[9]  J. J. Eisch, T. Dluzniewski, J. Org. Chem. 1989, 54, 1269.
         | Crossref | GoogleScholarGoogle Scholar |

[10]  H. Wei, Y. Li, K. Xiao, B. Cheng, H. Wang, L. Hu, H. Zhai, Org. Lett. 2015, 17, 5974.
         | Crossref | GoogleScholarGoogle Scholar | 26651162PubMed |

[11]  J. Marco-Contelles, E. Perez-Mayoral, A. Samadi, M. do Carmo Carreiras, E. Soriano, Chem. Rev. 2009, 109, 2652.
         | Crossref | GoogleScholarGoogle Scholar | 19361199PubMed |

[12]  Y.-Y. Yang, W.-G. Shou, Z.-B. Chen, D. Hong, Y.-G. Wang, J. Org. Chem. 2008, 73, 3928.
         | Crossref | GoogleScholarGoogle Scholar | 18399655PubMed |

[13]  X. Li, Z. Mao, Y. Wang, W. Chen, X. Lin, Tetrahedron 2011, 67, 3858.
         | Crossref | GoogleScholarGoogle Scholar |

[14]  M. Baumann, I. R. Baxendale, J. Org. Chem. 2015, 80, 10806.
         | Crossref | GoogleScholarGoogle Scholar | 26477591PubMed |

[15]  H. Saggadi, D. Luart, N. Thiebault, I. Polaert, L. Estel, C. Len, RSC Adv. 2014, 4, 21456.
         | Crossref | GoogleScholarGoogle Scholar |

[16]  J. Panteleev, R. Y. Huang, E. K. J. Lui, M. Lautens, Org. Lett. 2011, 13, 5314.
         | Crossref | GoogleScholarGoogle Scholar | 21916430PubMed |

[17]  A. Seoane, N. Casanova, N. Quiñones, J. L. Mascareñas, M. Gulías, J. Am. Chem. Soc. 2014, 136, 834.
         | Crossref | GoogleScholarGoogle Scholar | 24313353PubMed |

[18]  H. Jin, B. Tian, X. Song, J. Xie, M. Rudolph, F. Rominger, A. S. Hashmi, Angew. Chem. Int. Ed. 2016, 55, 12688.
         | Crossref | GoogleScholarGoogle Scholar |

[19]  Q. Gao, S. Liu, X. Wu, J. Zhang, A. Wu, J. Org. Chem. 2015, 80, 5984.
         | Crossref | GoogleScholarGoogle Scholar | 25973528PubMed |

[20]  T. Wezeman, S. Zhong, M. Nieger, S. Brase, Angew. Chem. Int. Ed. 2016, 55, 3823.
         | Crossref | GoogleScholarGoogle Scholar |

[21]  M. Rehan, G. Hazra, P. Ghorai, Org. Lett. 2015, 17, 1668.
         | Crossref | GoogleScholarGoogle Scholar | 25768127PubMed |

[22]  (a) For some representative examples of azepinoquinolines see: A. Hinschberger, S. Butt, V. Lelong, M. Boulouard, A. Dumuis, F. Dauphin, R. Bureau, B. Pfeiffer, P. Renard, S. Rault, J. Med. Chem. 2003, 46, 138.
         | Crossref | GoogleScholarGoogle Scholar | 12502367PubMed |
         (b) G. Lavielle, B. Cimetiere, T. Verbeuren, S. Simonet, J.-J. Descombes, EP Patent 1118610 2001.
      (c) A. Ghoshal, D. Yugandhar, J. B. Nanubolu, A. K. Srivastava, ACS Comb. Sci. 2017, 19, 600.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) J. Zhang, B. Xiong, X. Zhen, A. Zhang, Med. Res. Rev. 2009, 29, 272.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) A. K. Panday, R. Mishra, A. Jana, T. Parvin, L. H. Choudhury, J. Org. Chem. 2018, 83, 3624.
         | Crossref | GoogleScholarGoogle Scholar |
         (f) G. M. Shutske, R. C. Effland, EP Patent 287977 1994.
         (g) J. A. Groeper, X. Liao, Z. Lu, U.S. Patent 10 131 660 B2 2018.
      (h) M. Asencio, C. Hurtado-Guzmán, J. J. López, B. K. Cassels, P. Protais, A. Chagraoui, Bioorg. Med. Chem. 2005, 13, 3699.
         | Crossref | GoogleScholarGoogle Scholar |

[23]  S. R. Konda, B. R. Reguri, M. Kagga, Pharma Chem. 2014, 6, 250.

[24]  O. Di Pietro, E. Vicente-García, M. C. Taylor, D. Berenguer, E. Viayna, A. Lanzoni, I. Sola, H. Sayago, C. Riera, R. Fisa, M. Victòria Clos, B. Pérez, J. M. Kelly, R. Lavilla, D. Muñoz-Torrero, Eur. J. Med. Chem. 2015, 105, 120.
         | Crossref | GoogleScholarGoogle Scholar | 26479031PubMed |

[25]  (a) Y. K. Kang, D. Y. Kim, Chem. Commun. 2014, 50, 222.
         | Crossref | GoogleScholarGoogle Scholar |
      (b) S. B. Woo, D. Y. Kim, Beilstein J. Org. Chem. 2012, 8, 699.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) C. W. Suh, D. Y. Kim, Org. Lett. 2014, 16, 5374.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) Y. K. Kang, S. M. Kim, D. Y. Kim, J. Am. Chem. Soc. 2010, 132, 11847.
         | Crossref | GoogleScholarGoogle Scholar |

[26]  A. M. Zhidkova, V. G. Granik, R. G. Glushkov, T. F. Vlasova, O. S. Anisimova, T. A. Gus’kova, G. N. Pershin, Chem. Heterocycl. Compd. 1974, 10, 579. [Khim. Geterotsikl. Soedin. 1974, 670]
         | Crossref | GoogleScholarGoogle Scholar |

[27]  Y. Kuroki, H. Fujiwara, S. Nishino, I. Nakamura, H. Tokunaga, EP Patent 0430485 1991.

[28]  A. Cappelli, M. Anzini, S. Vomero, Heterocycles 1994, 38, 1265.
         | Crossref | GoogleScholarGoogle Scholar |

[29]  S. G. Michael, E. R. Charles, EP Patent 0 287 977 B1, 29 1994.

[30]  (a) M. E. Maier, Angew. Chem. Int. Ed. 2000, 39, 2073.
         | Crossref | GoogleScholarGoogle Scholar |
      (b) M. Kodama, K. Shimada, T. Takahashi, C. Kabuto, S. Itô, Tetrahedron Lett. 1981, 22, 4271.
         | Crossref | GoogleScholarGoogle Scholar |

[31]     (a) For reviews of hetero-Friedel–Crafts reactions and representative examples, see: J. Buckingham, K. H. Baggaley, A. D. Roberts, L. F. Szabó, Dictionary of Alkaloids (2nd edn) 2010 (CRC Press: Boca Raton, FL).
      (b) Y. Takayama, T. Yamada, S. Tatekabe, K. Nagasawa, Chem. Commun. 2013, 49, 6519.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) J. E. Taylor, M. D. Jones, J. M. J. Williams, D. Steven, Org. Lett. 2010, 12, 5740.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) A. Kubo, N. Saito, H. Yamato, K. Masubuchi, M. J. Nakamura, J. Org. Chem. 1988, 53, 4295.
         | Crossref | GoogleScholarGoogle Scholar |
         (e) D. C. Oniciu, in Comprehensive Heterocyclic Chemistry III (Eds A. R. Katritzky, C. A. Ramsden, E. F. V. Scriven, R. J. K. Taylor) 2008, Vol. 14, pp. 1–47 (Pergamon Press: New York, NY) and references cited therein.
      (f) Y.-L. Zhao, Q.-X. Lou, L.-S. Wang, W.-H. Hu, J.-L. Zhao, Angew. Chem. Int. Ed. 2017, 56, 338.
         | Crossref | GoogleScholarGoogle Scholar |

[32]  (a) H. A. K. Abd El-Aal, A. A. Khalaf, Aust. J. Chem. 2019, 72, 276.
         | Crossref | GoogleScholarGoogle Scholar |
      (b) H. A. K. Abd El-Aal, ARKIVOC 2018, 45.
      (c) H. A. K. Abd El-Aal, A. A. Khalaf, A. M. A. El-Khawaga, J. Heterocycl. Chem. 2014, 51, 262.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) H. A. K. Abd El-Aal, A. A. Khalaf, ARKIVOC 2019, 265.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) H. A. K. Abd El-Aal, A. A. Khalaf, Chem. Heterocycl. Compd. 2019, 55, 632.
         | Crossref | GoogleScholarGoogle Scholar |
      (f) H. A. K. Abd El-Aal, A. A. Khalaf, Polycycl. Aromat. Compd. 2013, 33, 331.
         | Crossref | GoogleScholarGoogle Scholar |

[33]     (a) L. R. C. Barclay, in Friedel-Crafts and Related Reactions (Ed. G. A. Olah) 1964, Vol. II, Ch. 22, pp. 785–977 (Wiley Interscience: New York, NY) and references therein.
         (b) R. M. Roberts, A. A. Khalaf, Friedel-Crafts Chemistry: A Century of Discovery 1984 (Marcel Dekker: New York, NY).
         (c) G. A. Olah, R. Krishnamurti, G. K. Surya Prakash, in Comprehensive Organic Synthesis (Eds B. M. Trost, I. Fleming) 1991, Vol. 3, pp. 293–335 (Pergamon Press: Oxford).
      (d) V. Terrasson, R. Marcia de Figueiredo, J. M. Campagne, Eur. J. Org. Chem. 2010, 2635.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) T. B. Poulsen, K. A. Jørgensen, Chem. Rev. 2008, 108, 2903.
         | Crossref | GoogleScholarGoogle Scholar |

[34]  L. G. Donaruma, W. Z. Heldt, Org. React. 1960, 11, 156.

[35]  M. J. Weiss, C. R. Hauser, J. Am. Chem. Soc. 1949, 71, 2023.
         | Crossref | GoogleScholarGoogle Scholar |

[36]  C. R. Hauser, B. E. Hudson, Org. React. 1942, 1, 266.

[37]  A. I. Mikhaleva, A. V. Ivanoc, E. V. Skital’tseva, I. A. Ushakov, A. M. Vasil’tsov, B. A. Trofimov, Synthesis 2009, 587.

[38]  H. E. Zimmerman, L. Ahramjian, J. Am. Chem. Soc. 1959, 81, 2086.
         | Crossref | GoogleScholarGoogle Scholar |

[39]  B. S. Furniss, A. J. Hannaford, P. W. G. Smith, A. R. Tatchell, Vogel’s Textbook of Practical Organic Chemistry (5th edn) 1989 (Addison Wesley/Longman: Essex).

[40]  L. Smith, Kgl. Fysiograf. Sällskap. Lun., Förh. 1948, 18, 3.[Chem. Abstr. 1950, 44, 1949e]

[41]  L. F. Fieser, F. C. Novello, J. Am. Ceram. Soc. 1940, 62, 1855.

[42]  (a) J. W. Huffman, V. J. Smith, L. W. Padgett, Tetrahedron 2008, 64, 2104.
         | Crossref | GoogleScholarGoogle Scholar | 19247425PubMed |
      (b) O. Ottoni, A. de V. F. Neder, A. K. B. Dias, R. P. A. Cruz, L. B. Aquino, Org. Lett. 2001, 3, 1005.

[43]  R. D. Shingare, R. Velayudham, J. R. Gawade, D. S. Reddy, Org. Lett. 2013, 15, 4556.
         | Crossref | GoogleScholarGoogle Scholar | 23964695PubMed |

[44]  A. G. Doyle, E. N. Jacobsen, Chem. Rev. 2007, 107, 5713.
         | Crossref | GoogleScholarGoogle Scholar | 18072808PubMed |

[45]  R. M. Silverstein, F. X. Webster, D. J. Kiemle, Spectrometric Identification of Organic Compounds (7th edn) 2005 (Wiley: Hoboken, NJ).