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Acid-catalyzed cascade rearrangement of 4-acetoxy-9-furylnaphtho[2,3-b]furans

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Abstract

Acid-catalyzed recyclization of 4-acetoxy-9-furylnaphtho[2,3-b]furans efficiently produced naphtho[1,2-b:3,4-b’]difurans. On the other hand, 4-aminonaphtho[2,3-b]furans failed to undergo the analogous recyclization into benzo[g]furo[2,3-e]indoles. The difference in behavior of these two types of substrates was explained by employing density functional theory calculations.

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Acknowledgments

Financial support was provided by the Russian Foundation for Basic Research (Grant 10-03-00254-a) and the Ministry of Education of the Permskii Krai. The authors would like to express their special thanks to Dr. V.E. Zavodnik for the accomplishment of the X-ray analysis.

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Authors and Affiliations

  1. Kuban State Technological University, Krasnodar, Russian Federation

    Alexander V. Fin’ko, Valery O. Babikov, Arkady S. Pilipenko & Alexander V. Butin

  2. North-Ossetian State University, Vladikavkaz, Russian Federation

    Vladimir T. Abaev

  3. Department of Chemistry, M. V. Lomonosov Moscow State University, Moscow, Russian Federation

    Igor V. Trushkov

  4. Dmitriy Rogachev Federal Research Center of Pediatric Hematology, Oncology, and Immunology, Moscow, Russian Federation

    Igor V. Trushkov

  5. Perm State University, Perm, Russian Federation

    Alexander V. Butin

Authors
  1. Alexander V. Fin’ko
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  2. Valery O. Babikov
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  3. Arkady S. Pilipenko
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  4. Vladimir T. Abaev
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  5. Igor V. Trushkov
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  6. Alexander V. Butin
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Corresponding authors

Correspondence to Igor V. Trushkov or Alexander V. Butin.

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Fin’ko, A.V., Babikov, V.O., Pilipenko, A.S. et al. Acid-catalyzed cascade rearrangement of 4-acetoxy-9-furylnaphtho[2,3-b]furans. Monatsh Chem 144, 1711–1723 (2013). https://doi.org/10.1007/s00706-013-1075-7

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  • DOI: https://doi.org/10.1007/s00706-013-1075-7

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