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Rearrangement–cyclization of dialkyl(4-hydroxybut-2-ynyl)meth-allyl- and dialkylcrotyl(4-hydroxy-but-2-ynyl) ammonium halides

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Chemistry of Heterocyclic Compounds Aims and scope

It was found that dialkyl(4-hydroxybut-2-ynyl)methallyl- and dialkylcrotyl(4-hydroxybut-2-ynyl)- ammonium halides undergo a Stevens rearrangement under the influence of aqueous alkali with transfer of the reaction center in the receiving group and inversion of the migrating group followed by cyclization to amino derivatives of furan.

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References

  1. E. O. Chukhadjian, A. S. Gabrielyan, A. R. Gevorkyan, H. A. Panosyan, T. D. Karapetyan, Khim. Geterotsikl. Soedin., 354 (2009). [Chem. Heterocycl. Comp., 45, 284 (2009)].

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  2. E. O. Chukhadjiyan, A. R. Gevorkyan, El. O. Chukhadjiyan, K. G. Shakhatuni, Zh. Org. Khim., 36, 1304 (2000).

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Authors and Affiliations

  1. Institute of Organic Chemistry, Scientific–Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia, Yerevan, 0014, Republic of Armenia

    E. O. Chukhajian, A. S. Gabrielyan, El. O. Chukhajian & K. G. Shahkhatuni

  2. Molecular Structure Research Center, Scientific–Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia, Yerevan, 0014, Republic of Armenia

    H. A. Panosyan

Authors
  1. E. O. Chukhajian
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  2. A. S. Gabrielyan
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  3. El. O. Chukhajian
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  4. K. G. Shahkhatuni
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  5. H. A. Panosyan
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Corresponding author

Correspondence to A. S. Gabrielyan.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1622–1628, November, 2009.

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Chukhajian, E.O., Gabrielyan, A.S., Chukhajian, E.O. et al. Rearrangement–cyclization of dialkyl(4-hydroxybut-2-ynyl)meth-allyl- and dialkylcrotyl(4-hydroxy-but-2-ynyl) ammonium halides. Chem Heterocycl Comp 45, 1302–1307 (2009). https://doi.org/10.1007/s10593-010-0425-1

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  • DOI: https://doi.org/10.1007/s10593-010-0425-1

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