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Synthesis of cinnoline 1-oxides by the reaction of ortho-fluoronitrobenzenes with enediamines

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Abstract

Reaction of α-carbonylacetamidines existing in the enediamine tautomeric form with the substituted ortho-fluoronitrobenzene afforded products of the replacement of the fluorine by the α-C atom of amidine. The latter underwent cyclization into cinnoline 1-oxides on treatment with sodium hydride.

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References

  1. D. V. Dar’in, S. I. Selivanov, P. S. Lobanov, A. A. Potekhin, Khim. Geterotsikl. Soedin., 2004, 1036 [Chem. Heterocycl. Compd. (Engl. Transl.), 2004, 40, 888].

    Google Scholar 

  2. S. G. Ryazanov, S. I. Selivanov, D. V. Dar’in, P. S. Loban- ov, A. A. Potekhin, Zh. Org. Khim., 2008, 44, 292 [Russ. J. Org. Chem. (Engl. Transl.), 2008, 44, 288].

    Google Scholar 

  3. I. I. Eliseev, Jr., D. V. Dar’in, S. I. Selivanov, P. S. Lobanov, A. A. Potekhin, Khim. Geterotsikl. Soedin., 2008, 567 [Chem. Heterocycl. Compd. (Engl. Transl.), 2008, 44, 442].

    Google Scholar 

  4. S. F. Yan, D. V. Dar’in, P. S. Lobanov, A. A. Potekhin, Khim. Geterotsikl. Soedin., 2008, 585 [Chem. Heterocycl. Compd. (Engl. Transl.), 2008, 44, 457].

    Google Scholar 

  5. D. V. Dar’in, S. G. Ryazanov, S. I. Selivanov, P. S. Lobanov, A. A. Potekhin, Khim. Geterotsikl. Soedin., 2008, 589 [Chem. Heterocycl. Compd. (Engl. Transl.), 2008, 44, 461].

    Google Scholar 

  6. C. Huang, S.-J. Yan, X.-H. Zeng, X.-Y. Dai, Y. Zhang, C. Qing, J. Lin, Eur. J. Med. Chem., 2011, 46, 1172.

    Article  CAS  Google Scholar 

  7. P. N. Preston, G. Tennant, Chem. Rev., 1972, 72, 627.

    Article  CAS  Google Scholar 

  8. Q. Xia, L. Zhang, J. Zhang, R. Sheng, B. Yang, Q. He, Y. Hu, Eur. J. Med. Chem., 2011, 46, 919.

    Article  CAS  Google Scholar 

  9. M. P. Hay, K. O. Hicks, K, Pchalek, H. H. Lee, A. Blaser, F. B. Pruijn, R. F. Anderson, S. S. Shinde, W. R. Wilson, W. A. Denny, J. Med. Chem., 2008, 51, 6853.

    Article  CAS  Google Scholar 

  10. G. B. W. L. Ligthart, D. Guo, A. L. Spek, H. Kooijman, H. Zuilhof, R. P. Sijbesma, J. Org. Chem., 2008, 73, 111.

    Article  CAS  Google Scholar 

  11. M. Scobie, G. Tennant, J. Chem. Soc., Chem. Commun., 1993, 1756.

  12. M. Scobie, G. Tennant, J. Chem. Soc., Chem. Commun., 1994, 2451.

  13. O. V. Vinogradova, I. A. Balova, Khim. Geterotsikl. Soedin., 2008, 643 [Chem. Heterocycl. Compd. (Engl. Transl.), 2008, 44, 501].

  14. A. Slevin, T. Koolmeister, M. Scobie, Chem. Commun., 2007, 2506.

  15. M. J. Haddadin, R. M. B. Zerdan, M. J. Kurth, J. C. Fettinger, Org. Lett., 2010, 12, 5502.

    Article  CAS  Google Scholar 

  16. A. V. Vypolzov, S. F. Yan, D. V. Dar’in, P. S. Lobanov, Khim. Geterotsikl. Soedin., 2010, 789 [Chem. Heterocycl. Compd. (Engl. Transl.), 2010, 46, 634].

    Google Scholar 

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Correspondence to A. V. Vypolzov.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 0873-0876, April, 2012.

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Vypolzov, A.V., Dar’in, D.V. & Lobanov, P.S. Synthesis of cinnoline 1-oxides by the reaction of ortho-fluoronitrobenzenes with enediamines. Russ Chem Bull 61, 877–880 (2012). https://doi.org/10.1007/s11172-012-0123-5

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  • DOI: https://doi.org/10.1007/s11172-012-0123-5

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