The cyclization reaction of ortho-ethynylbenzaldehyde derivatives into isoquinoline derivatives

Takao Sakamoto; Atsushi Numata; Yoshinori Kondo

doi:10.1248/cpb.48.669

The cyclization reaction of ortho-ethynylbenzaldehyde derivatives into isoquinoline derivatives

Takao Sakamoto, Atsushi Numata, Yoshinori Kondo

PHA - Molecular Pharmaceutical Science

Research output: Contribution to journal › Article › peer-review

23 Citations (Scopus)

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.

Original language	English
Pages (from-to)	669-672
Number of pages	4
Journal	Chemical and Pharmaceutical Bulletin
Volume	48
Issue number	5
DOIs	https://doi.org/10.1248/cpb.48.669
Publication status	Published - 2000 May

Keywords

2-ethynylbenzaldehyde
Cyclization
Isoquinoline
N-oxide
Palladium- catalyzed reaction

ASJC Scopus subject areas

Chemistry(all)
Drug Discovery

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author = "Takao Sakamoto and Atsushi Numata and Yoshinori Kondo",

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AU - Sakamoto, Takao

AU - Numata, Atsushi

AU - Kondo, Yoshinori

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Y1 - 2000/5

N2 - 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.

AB - 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.

KW - 2-ethynylbenzaldehyde

KW - Cyclization

KW - Isoquinoline

KW - N-oxide

KW - Palladium- catalyzed reaction

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The cyclization reaction of ortho-ethynylbenzaldehyde derivatives into isoquinoline derivatives

Abstract

Keywords

ASJC Scopus subject areas

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