Studies on Diazepine. XXX. : Addition Reactions of Monocyclic Diazepines with Dimethyl Acetylenedicarboxylate Involving Diazonine Intermediates

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The reaction of the 1H-1,3-diazepines (8a-c) with dimethyl acetylenedicarboxylate (DMAD) gave the 3a, 7a-dihydropyrrolo[3,2-b]pyridines (9), probably via the 1,5-diazonine intermediates 11 derived from the initially formed [2+2]π cycloadducts 10. Similarly, the 1H-1,2-diazepines (15a-c), upon treatment with DMAD, produced the 3a, 7a-dihydroindazoles (20), presumably via the [2+2]π cycloadducts 18 and the 1,2-diazonines 19 successively, but hte dihydroindazoles (20) further reacted with the reagent to give the dimethyl phthalates (16) and the pyrazole (17) as the final products via the [4+2]π cycloadducts 21. These results are the first examples of the reaction of fully unsaturated seven-membered heterocyclic rings with acetylenes.

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Details 詳細情報について

  • CRID
    1573105977298668416
  • NII Article ID
    110003626800
  • NII Book ID
    AA00602100
  • ISSN
    00092363
  • Text Lang
    en
  • Data Source
    • CiNii Articles

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