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The cyclization reaction of ortho-ethynylbenzaldehyde derivatives into isoquinoline derivatives
T Sakamoto1, A Numata, Y Kondo
1Graduate School of Pharmaceutical Sciences, Tohoku University, Sendai, Japan. Sakamoto@mail.pharm.tohoku.ac.jp
Chemical & Pharmaceutical Bulletin
|May 24, 2000
Abstract:
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.