Russian Journal of Organic Chemistry

, Volume 46, Issue 1, pp 113–116 | Cite as

Three-component condensation of o- and p-methoxytoluenes with isobutyraldehyde and α-substituted benzyl cyanides. Synthetic approach to analogs of natural alkaloids

  • Yu. V. Shklyaev
  • M. A. El’tsov
  • O. A. Maiorova
Review

Abstract

Three-component condensation of o(p)-methoxytoluene with isobutyraldehyde and α-substiituted benzyl cyanides gave 8-acetyl-3,6,6-trimethyl-5,6,7,12b-tetrahydrodibenzo[d,f]indol-2(1H)-one or 8-acetyl- 1,6,6-trimethyl-3,4,5,6,7,12b-hexahydrodibenzo[d,f]indol-3-one. Analogous reaction of p-methoxytoluene with isobutyraldehyde and 1-phenylcyclopentane-1-carbonitrile afforded 1’,6,6-trimethyl-3,4,5,6,7,12b-hexahy- drospiro[cyclopentane-1’,8-dibenzo[d,f]indol]-3-ones.

Keywords

Vinyl Ether Isobutyraldehyde Benzyl Cyanide Dihydropyrrole Morphinane Alkaloid 

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Copyright information

© Pleiades Publishing, Ltd. 2010

Authors and Affiliations

  • Yu. V. Shklyaev
    • 1
  • M. A. El’tsov
    • 1
  • O. A. Maiorova
    • 1
  1. 1.Institute of Technical Chemistry, Ural DivisionRussian Academy of SciencesPermRussia

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