Jump to main content
Jump to site search
Publishing
Advanced

Issue 8, 1994
Previous Article Next Article

Synthesis of 1,6-methano[10]annulenopyridines by tandem aza-Wittig reaction/electrocyclisation

Thomas Bohn,  Walter Kramer,  Richard Neidlein  and  Hans Suschitzky 

Abstract

Iminophosphoranes 1(X = PPh3) derived from the corresponding 1,6-methano[10]annulenes have been made to react with isothiocyanates and also with aromatic aldehydes to give, by an aza-Wittig reaction followed by cyclisation, novel 1,6-methano[10]annulenopyridines of structural types 2 and 6. Aza-Wittig reactions of the 2-triphenylphosphoranylideneamino derivative 3(X = PPh3) with aromatic aldehydes or isothiocyanates led to the Schiff's bases 3(X = CHAr) or carbodiimides (X = C[double bond, length half m-dash]NAr) respectively. The latter on treatment with enamines gave, by a Diels–Alder cyclisation, the annuleno[2,3-b]pyridines 12.

Back to tab navigation
Download options Please wait...

Article type: Paper
DOI: 10.1039/P19940000947
Citation: J. Chem. Soc., Perkin Trans. 1, 1994,0, 947-951
  •   Request permissions

    Synthesis of 1,6-methano[10]annulenopyridines by tandem aza-Wittig reaction/electrocyclisation

    T. Bohn, W. Kramer, R. Neidlein and H. Suschitzky, J. Chem. Soc., Perkin Trans. 1, 1994, 0, 947
    DOI: 10.1039/P19940000947

    If you are not the author of this article and you wish to reproduce material from it in a third party non-RSC publication you must formally request permission using RightsLink. Go to our Instructions for using RightsLink page for details.

    Authors contributing to RSC publications (journal articles, books or book chapters) do not need to formally request permission to reproduce material contained in this article provided that the correct acknowledgement is given with the reproduced material.

    Reproduced material should be attributed as follows:

    • For reproduction of material from NJC:
      Reproduced from Ref. XX with permission from the Centre National de la Recherche Scientifique (CNRS) and The Royal Society of Chemistry.
    • For reproduction of material from PCCP:
      Reproduced from Ref. XX with permission from the PCCP Owner Societies.
    • For reproduction of material from PPS:
      Reproduced from Ref. XX with permission from the European Society for Photobiology, the European Photochemistry Association, and The Royal Society of Chemistry.
    • For reproduction of material from all other RSC journals and books:
      Reproduced from Ref. XX with permission from The Royal Society of Chemistry.

    If the material has been adapted instead of reproduced from the original RSC publication "Reproduced from" can be substituted with "Adapted from".

    In all cases the Ref. XX is the XXth reference in the list of references.

    If you are the author of this article you do not need to formally request permission to reproduce figures, diagrams etc. contained in this article in third party publications or in a thesis or dissertation provided that the correct acknowledgement is given with the reproduced material.

    Reproduced material should be attributed as follows:

    • For reproduction of material from NJC:
      [Original citation] - Reproduced by permission of The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC
    • For reproduction of material from PCCP:
      [Original citation] - Reproduced by permission of the PCCP Owner Societies
    • For reproduction of material from PPS:
      [Original citation] - Reproduced by permission of The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC
    • For reproduction of material from all other RSC journals:
      [Original citation] - Reproduced by permission of The Royal Society of Chemistry

    If you are the author of this article you still need to obtain permission to reproduce the whole article in a third party publication with the exception of reproduction of the whole article in a thesis or dissertation.

    Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Search articles by author

Spotlight

Advertisements