Reactions of 4-methylidenedioxolan-2-ones with 2-methyltryptamines. Synthesis of core analogs of aurantioclavine |
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| Authors: | I Yu Titov N B Chernysheva A A Bogolyubov V V Semenov V G Nenajdenko E S Balenkova |
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| Institution: | (1) N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation;(2) Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory, 119992 Moscow, Russian Federation |
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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., oxazolo3",4":1,2]azepino5,4,3-cd]indole, which are core analogs of aurantioclavine, were prepared. |
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| Keywords: | 4-methylidenedioxolan-2-ones 2-methyltryptamines 4-hydroxyoxazolidin-2-ones intramolecular amidoalkylation 6 7 11 11a-tetrahydro-4H-oxazolo[3" 4":1 2]azepino[5 4 3-cd]indole aurantioclavine |
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