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1,5-Electrocyclization of 1-alkyl- 3-[(2Z)-2,4-diaryl-4-oxobut-2-en-1-yl]-1H-benzimidazol-3-ium bromides

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Chemistry of Heterocyclic Compounds Aims and scope

Cyclization of 1-alkyl-3-[(2Z)-2,4-diaryl-4-oxobut-2-en-1-yl]-1H-benzimidazol-3-ium bromides occurs in the presence of MeONa at a reduced temperature of 5–10°C via a 1,5-electrocyclization mechanism to give 3a,4-dihydro-3H-pyrrolo[1,2-a]benzimidazoles. These are unstable under the reaction conditions and are readily converted to {1-[2-(alkylamino)phenyl]-4-phenyl-1H-pyrrol-3-yl}(phenyl)methanones.

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References

  1. V. G. Kartsev (editor), Selected Methods of Synthesis and Modification of Heterocycles [in Russian], Vol. 1, IBS Press, Moscow (2003), p. 393.

  2. L. Potikha, V. Kovtunenko, A. Turelyk, A. Turov, and A. Tolmachev, Synth. Commun., 38, 2016 (2008).

    Article  Google Scholar 

  3. L. M. Potikha, A. R. Turelyk, and V. A. Kovtunenko, Khim. Geterotsikl. Soedin., 95 (2010). [Chem. Heterocycl. Comp., 46, 82 (2010)].

    Google Scholar 

  4. X-c. Zhang and W-y. Huang, Tetrahedron Lett., 38, 4827 (1997).

    Article  CAS  Google Scholar 

  5. X-c. Zhang and W-y. Huang, Tetrahedron, 54, 12465 (1998).

    Article  CAS  Google Scholar 

  6. E. Pohjala, Tetrahedron Lett., 13, 2585 (1972).

    Article  Google Scholar 

  7. Y. Tamura, N. Tsujimoto, Y. Sumida, and M. Ikeda, Tetrahedron, 28, 21 (1972).

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Taras Shevchenko National University, 64 Volodymyrs’ka St., Kyiv, 01033, Ukraine

    L. M. Potikha, A. R. Turelyk & V. A. Kovtunenko

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  1. L. M. Potikha
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  2. A. R. Turelyk
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  3. V. A. Kovtunenko
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Correspondence to L. M. Potikha.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 552–556, April, 2011.

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Potikha, L.M., Turelyk, A.R. & Kovtunenko, V.A. 1,5-Electrocyclization of 1-alkyl- 3-[(2Z)-2,4-diaryl-4-oxobut-2-en-1-yl]-1H-benzimidazol-3-ium bromides. Chem Heterocycl Comp 47, 452–455 (2011). https://doi.org/10.1007/s10593-011-0780-6

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  • DOI: https://doi.org/10.1007/s10593-011-0780-6

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