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Reactions of 4-methylidenedioxolan-2-ones with 2-methyltryptamines. Synthesis of core analogs of aurantioclavine

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Abstract

4-Hydroxy-4,5,5-trimethyl-3-[2-(2-methyl-7-R-1H-indol-3-yl)ethyl]-1,3-oxazolidin-2-ones (R = H or Alk), which were synthesized from 4-methylidene-1,3-dioxolan-2-one and substituted 2-methyltryptamines, undergo intramolecular amidoalkylation when treated with polyphosphoric acid. First representatives of a new heterocyclic system, viz., oxazolo[3",4":1,2]azepino[5,4,3-cd]indole, which are core analogs of aurantioclavine, were prepared.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    I. Yu. Titov, N. B. Chernysheva, A. A. Bogolyubov & V. V. Semenov

  2. Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory, 119992, Moscow, Russian Federation

    V. G. Nenajdenko & E. S. Balenkova

Authors
  1. I. Yu. Titov
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  2. N. B. Chernysheva
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  3. A. A. Bogolyubov
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  4. V. V. Semenov
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  5. V. G. Nenajdenko
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  6. E. S. Balenkova
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Titov, I.Y., Chernysheva, N.B., Bogolyubov, A.A. et al. Reactions of 4-methylidenedioxolan-2-ones with 2-methyltryptamines. Synthesis of core analogs of aurantioclavine. Russian Chemical Bulletin 53, 569–572 (2004). https://doi.org/10.1023/B:RUCB.0000035639.83432.20

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  • DOI: https://doi.org/10.1023/B:RUCB.0000035639.83432.20

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