Chemical and Pharmaceutical Bulletin p. 669 - 672 (2000)
Update date:2022-08-17
Topics:
Sakamoto, Takao
Numata, Atsushi
Kondo, Yoshinori
In order to elucidate the reaction mechanism of the cyclization between an ethynyl group and an imino group at the ortho-position on an aromatic ring to afford isoquinolines, reaction of 2-ethynylbenzaldehydes under various conditions was examined. It is concluded that reaction proceeds via an ionic process and the isoquinoline 4-hydrogen atom derives from the solvent. In addition, it was found that 2-ethynylbenzaldehyde O-methyloximes underwent cyclization in the presence of primary and secondary alcohols to give 3- substituted isoquinolines.
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