Treatment of the N-aminopyridinium salts (5a-e) prepared from 2-ethynylpyridines (4) with potassium carbonate resulted in an intramolecular cyclization to give the corresponding 3-azaindolizines (6) (pyrazolo [2, 3-a] pyridines), presumably via the ionic intermediates (8) and (9). Similarly, pyrazolo [2, 3-a] quinolines (13a-c), pyrazolo [3, 2-a] isoquinolines (16a-c), and pyrazolo [2, 3-b] isoquinolines (19a-c) were obtained from the corresponding ethynylquinolines (11) or ethynylisoquinolines (14, 17) via the N-amino salts (12, 15, or 18).
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