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Convenient synthesis of 12-methyl[1]benzoxepino[3,4-b]quinolin-13(6H)-ones

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Chemistry of Heterocyclic Compounds Aims and scope

In this work, a construction of 12-methyl[1]benzoxepino[3,4-b]quinolin-13(6H)-ones, structurally intriguing hybrid molecules consisting of fused 4-methylquinoline and 1-benzoxepin-5-one units, has been successfully achieved via a two-step procedure, involving the onepot synthesis of 2-(aryloxymethyl)-4-methylquinoline-3-carboxylic acids followed by their intramolecular Friedel–Crafts cyclization reaction. Our synthetic protocol described here could be attractive as it is simple, easy to handle and does not involve the use of expensive reagents or catalysts.

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References

  1. Huang, S. T.; Kuo, H. S.; Chen, C. T. Tetrahedron Lett. 2001, 42, 7473.

    Article  CAS  Google Scholar 

  2. Bruder, M.; Haseler, P. L.; Muscarella, M.; Lewis, W.; Moody, C. J. J. Org. Chem. 2010, 75, 353.

    Article  CAS  PubMed  Google Scholar 

  3. Pettit, G. R.; Numata, A.; Iwamoto, C.; Usami, Y.; Yamada, T.; Ohishi, H.; Cragg, G. M. J. Nat. Prod. 2006, 69, 323.

    Article  CAS  PubMed  Google Scholar 

  4. Boonphong, S.; Puangsombat, P.; Baramee, A.; Mahidol, C.; Ruchirawat, S.; Kittakoop, P. J. Nat. Prod. 2007, 70, 795.

    Article  CAS  PubMed  Google Scholar 

  5. Sarkhel, S.; Sharon, A.; Trivedi, V.; Maulik, P. R.; Singh, M. M.; Venugopalan, P.; Ray, S. Bioorg. Med. Chem. 2003, 11, 5025.

    Article  CAS  PubMed  Google Scholar 

  6. Saidachary, G.; Prasad, K. V.; Divya, D.; Singh, A.; Ramesh, U.; Sridhar, B.; Raju, B. C. Eur. J. Med. Chem. 2014, 76, 460.

    Article  CAS  PubMed  Google Scholar 

  7. Kahnberg, P.; Sterner, O. Tetrahedron 2001, 57, 7181.

    Article  CAS  Google Scholar 

  8. Lee, S. H.; Van, H. T. M.; Yang, S. H.; Lee, K. T.; Kwon, Y.; Cho, W. J. Bioorg. Med. Chem. Lett. 2009, 19, 2444.

    Article  CAS  Google Scholar 

  9. Liu, J. H.; Steigel, A.; Reininger, E.; Bauer, R. J. Nat. Prod. 2000, 63, 403.

    Article  CAS  PubMed  Google Scholar 

  10. Staben, S. T.; Siu, M.; Goldsmith, R.; Olivero, A. G.; Do, S.; Burdick, D. J.; Heffron, T. P.; Dotson, J.; Sutherlin, D. P.; Zhu, B. Y.; Tsui, V.; Le, H.; Lee, L.; Lesnick, J.; Lewis, C.; Murray, J. M.; Nonomiya, J.; Pang, J.; Prior, W. W.; Salphati, L.; Rouge, L.; Sampath, D.; Sideris, S.; Wiesmann, C.; Wu, P. Bioorg. Med. Chem. Lett. 2011, 21, 4054.

    Article  CAS  PubMed  Google Scholar 

  11. Kamboj, R. C.; Jindal, P.; Kumar, D.; Khullar, S.; Mandal, S. K. J. Photochem. Photobiol. A: Chem. 2014, 278, 31.

    Article  CAS  Google Scholar 

  12. Rao Mangina, N. S. V. M.; Suresh, S.; Sridhar, B.; Karunakar, G. V. Org. Biomol. Chem. 2016, 14, 3526.

    Article  CAS  Google Scholar 

  13. Rao Mangina, N. S. V. M.; Kadiyala, V.; Guduru, R.; Goutham, K.; Sridhar, B.; Karunakar, G. V. Org. Lett. 2017, 19, 282.

    Article  CAS  Google Scholar 

  14. Johnson, O. H.; Hamilton, C. S. J. Am. Chem. Soc. 1941, 63, 2864.

    Article  CAS  Google Scholar 

  15. LaMontagne, M. P.; Dagli, D.; Khan, M. S.; Blumbergs, P. J. Med. Chem. 1980, 23, 981.

    Article  CAS  PubMed  Google Scholar 

  16. Urbina, J. M.; Cortés, J. C. G.; Palma, A.; López, S. N.; Zacchino, S. A.; Enriz, R. D.; Ribas, J. C.; Kouznetzov, V. V. Bioorg. Med. Chem. 2000, 8, 691.

    Article  CAS  PubMed  Google Scholar 

  17. Jain, R.; Vaitilingam, B.; Nayyar, A.; Palde, P. B. Bioorg. Med. Chem. Lett. 2003, 13, 1051.

    Article  CAS  PubMed  Google Scholar 

  18. Ulven, T.; Little, P. B.; Receveur, J. M.; Frimurer, T. M.; Rist, Ø.; Nørregaard, P. K.; Högberg, T. Bioorg. Med. Chem. Lett. 2006, 16, 1070.

    Article  CAS  PubMed  Google Scholar 

  19. Li, A.; Huang, C.; Luo, C. W.; Li, L. J.; Yi, W. J.; Liu, T. W.; Chao, Z. S. Catal. Commun. 2017, 98, 13.

    Article  CAS  Google Scholar 

  20. Dolle, R. E.; Nelson, K. H. J. Comb. Chem. 1999, 1, 235.

    Article  CAS  PubMed  Google Scholar 

  21. Gao, W. T.; Lin, G. H.; Li, Y.; Tao, X. Y.; Liu, R.; Sun, L. J. Beilstein J. Org. Chem. 2012, 8, 1849.

    CAS  Google Scholar 

  22. Gao, W. T.; Xing, X. D.; Li, Y.; Lan, S. Tetrahedron 2014, 70, 2180.

    Article  CAS  Google Scholar 

  23. Gao, W. T.; Fu, X. B.; Zhang, X. F.; Zhao, Y. N.; Wang, D. F.; Li, Y. Tetrahedron Lett. 2016, 57, 4145.

    Article  CAS  Google Scholar 

  24. Li, Y.; Li, K.; Gao, W. T. Chem. Heterocycl. Compd. 2016, 52, 200. [Khim. Geterotsikl. Soedin. 2016, 52, 200.]

  25. Li, Y.; Wang, Y.; Zou, H. T. Mol. Diversity 2017, 21, 463.

    Article  CAS  Google Scholar 

  26. Jida, M.; Deprez, B. New J. Chem. 2012, 36, 869.

    CAS  Google Scholar 

  27. Ryabukhin, S. V.; Volochnyuk, D. M.; Plaskon, A. S.; Naumchik, V. S.; Tolmachev, A. A. Synthesis 2007, 1214.

  28. Degtyarenko, A. S.; Tolmachev, A. A.; Volovenko, Y. M.; Tverdokhlebov, A. V. Synthesis 2007, 3891.

  29. Xu, J.; Wang, D. L.; Liu, Z. P.; Zhang, K. X.; Ma, W.; Liu, B. Heterocycles 2017, 94, 1055.

    Article  CAS  Google Scholar 

  30. Nammalwar, B.; Murie, M.; Fortenberry, C.; Bunce, R. A. Tetrahedron Lett. 2014, 55, 3181.

    Article  CAS  Google Scholar 

  31. Eaton, P. E.; Carlson, G. R.; Lee, J. T. J. Org. Chem. 1973, 38, 4071.

    Article  CAS  Google Scholar 

  32. Meesala, R.; Nagarajan, R. Tetrahedron Lett. 2010, 51, 422.

    Article  CAS  Google Scholar 

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The project was financially supported by the National Natural Science Foundation of China (Nos. 21476028 and 21402011) and the Natural Science Foundation of Liaoning Province (No. 201602006).

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Authors and Affiliations

  1. Institute of Superfine Chemicals, Bohai University, Jinzhou, 121000, China

    Yu Wang, Mingqin Chang, Hong Zhang & Yang Li

Authors
  1. Yu Wang
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  2. Mingqin Chang
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  3. Hong Zhang
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  4. Yang Li
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Corresponding author

Correspondence to Yang Li.

Additional information

Supplementary information file containing the 1H and 13C NMR spectra of compounds 7a–l and 6a–l is available at the journal website at http://link.springer.com/journal/10593.

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(6), 650–657

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Wang, Y., Chang, M., Zhang, H. et al. Convenient synthesis of 12-methyl[1]benzoxepino[3,4-b]quinolin-13(6H)-ones. Chem Heterocycl Comp 54, 650–657 (2018). https://doi.org/10.1007/s10593-018-2322-y

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  • DOI: https://doi.org/10.1007/s10593-018-2322-y

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