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Synthesis of 2-amino-4H-3,1-benzoxazines and 2-amino-4H-3,1-benzothiazines by the rearrangement of o-cyclopropylphenylureas and o-cyclopropylphenylthioureas

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Chemistry of Heterocyclic Compounds Aims and scope

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Abstract

Syntheses are reported for 2-cyclopropylphenylureas and 2-cyclopropylphenylthioureas and the behavior of these compounds was studied under conditions for the acid-catalyzed opening of the cyclopropyl ring. Upon the action of concentrated sulfuric acid or trifluoroacetic acid, these ureas and thioureas can undergo rearrangement to the corresponding 3,1-benzoxazines and 3,1-benzothiazines.

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References

  1. R. Ya. Levina, V. N. Kostin, and V. A. Tartakovskii, Zh. Obshch. Khim., 27, 881 (1957).

    CAS  Google Scholar 

  2. R. J. Ouellette, R. D. Robins, and A. South, J. Am. Chem. Soc., 90, 1619 (1968).

    Article  CAS  Google Scholar 

  3. Yu. S. Shabarov, S. S. Mochalov, T. S. Oretskaya, and V. V. Karpova, J. Organomet. Chem., 150, 7 (1978).

    Article  CAS  Google Scholar 

  4. Yu. S. Shabarov, S. S. Mochalov, S. A. Blagodatskikh, and R. Ya. Levina, Vestn. Moskovsk. Gos. Univ., Ser. Khim., 6, 689 (1972).

    Google Scholar 

  5. Yu. S. Shabarov, S. S. Mochalov, S. A. Blagodatskikh, and R. Ya. Levina, Zh. Org. Khim., 6, 2038 (1970).

    CAS  Google Scholar 

  6. S. Danishefsky, Acc. Chem. Res., 12, 66 (1979).

    Article  CAS  Google Scholar 

  7. H. N. Yong, M.-Y. Hon, C.-W. Tse, and Yu.-C. Yip, Chem. Rev., 89, 165 (1989).

    Article  Google Scholar 

  8. H.-V. Reissig and R. Zimmer, Chem. Rev., 103, 1151 (2003).

    Article  CAS  Google Scholar 

  9. S. S. Mochalov and R. A. Gazzaeva, Khim. Geterotsikl. Soedin., 1123 (2003). [Chem. Heterocycl. Comp., 39, 975 (2003)].

    Google Scholar 

  10. Y.-H. Wang and M. Shi, Tetrahedron, 62, 2420 (2006).

    Article  CAS  Google Scholar 

  11. M. Yu and B. L. Padenkopf, Tetrahedron, 61, 321 (2005).

    Article  CAS  Google Scholar 

  12. Yu. S. Shabarov, S. S. Mochalov, and I. P. Stepanov, Dokl. Akad. Nauk SSSR, 189, 1028 (1969).

    CAS  Google Scholar 

  13. S. S. Mochalov, A. N. Fedotov, A. A. Borisenko, V. V. Tkachev, G. V. Shilov, A. N. Utenyshev, S. M. Aldoshin, and N. S. Zefirov, Dokl. Akad. Nauk, 391, 646 (2003).

    Google Scholar 

  14. S. S. Mochalov, R. A. Gazzaeva, A. N. Fedotov, Yu. S. Shabarov, and N. S. Zefirov, Khim. Geterotsikl. Soedin., 922 (2003). [Chem. Heterocycl. Comp., 39, 794 (2003)].

    Google Scholar 

  15. H. Hart and C. Levitt, J. Org. Chem., 24, 1261 (1959).

    Article  CAS  Google Scholar 

  16. Yu. S. Shabarov, V. K. Potapov, and R. Ya. Levina, Zh. Obshch. Khim., 34, 3127 (1964).

    CAS  Google Scholar 

  17. Yu. S. Shabarov and S. S. Mochalov, Zh. Org. Khim., 8, 2085 (1972).

    CAS  Google Scholar 

  18. T. G. Kutateladze, A. N. Fedotov, S. S. Mochalov, and Yu. S. Shabarov, USSR Inventor’s Certificate 1502570; Byul. Izobr., 31, 134 (1989).

    Google Scholar 

  19. A. N. Fedotov, I. N. Shishkina, T. G. Kutateladze, S. S. Mochalov, and Yu. S. Shabarov, Khim. Geterotsikl. Soedin., 1063 (1987). [Chem. Heterocycl. Comp., 23, 849 (1987)].

    Google Scholar 

  20. J. Gonda and P. Kristian, Coll. Czech. Chem. Commun., 51, 2802, 2810 (1986).

    CAS  Google Scholar 

  21. J. Gonda and M. Barnikol, Coll. Czech. Chem. Commun., 55, 752 (1990).

    Article  CAS  Google Scholar 

  22. P. Molina, A. Arques, and A. Molina, Synthesis, 21 (1991).

  23. A. Hari and B. L. Willer, Org. Lett., 2, 3667 (2000).

    Article  CAS  Google Scholar 

  24. A. N. Fedotov, E. V. Trofimova, V. A. Sidorov, K. A. Potekhin, V. A. Romanov, S. S. Mochalov, and N. S. Zefirov, Dokl. Akad. Nauk, 405, 65 (2005).

    Google Scholar 

  25. P. J. Garatt, C. J. Hobbs, and R. Wrigglesworth, Tetrahedron, 45, 829 (1989).

    Article  Google Scholar 

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Authors and Affiliations

  1. M. V. Lomonosov Moscow State University, Moscow, 119992, Russia

    A. N. Fedotov, E. V. Trofimova, V. A. Romanov, S. S. Mochalov, Yu. S. Shabarov & N. S. Zefirov

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  1. A. N. Fedotov
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  2. E. V. Trofimova
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  3. V. A. Romanov
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  4. S. S. Mochalov
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  5. Yu. S. Shabarov
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  6. N. S. Zefirov
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Correspondence to A. N. Fedotov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 115–126, January, 2008.

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Fedotov, A.N., Trofimova, E.V., Romanov, V.A. et al. Synthesis of 2-amino-4H-3,1-benzoxazines and 2-amino-4H-3,1-benzothiazines by the rearrangement of o-cyclopropylphenylureas and o-cyclopropylphenylthioureas. Chem Heterocycl Comp 44, 96–105 (2008). https://doi.org/10.1007/s10593-008-0006-8

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  • DOI: https://doi.org/10.1007/s10593-008-0006-8

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