Condensed Heteroaromatic Ring Systems. VIII.1) Synthesis of 3-Substituted Isocoumarins from o-Halobenzoic Acid Derivatives

Takao Sakamoto; Masayuki An-Naka; Yoshinori Kondo; Hiroshi Yamanaka

doi:10.1248/cpb.34.2754

Condensed Heteroaromatic Ring Systems. VIII.₁₎ Synthesis of 3-Substituted Isocoumarins from o-Halobenzoic Acid Derivatives

Takao Sakamoto, Masayuki An-Naka, Yoshinori Kondo, Hiroshi Yamanaka

PHA - Molecular Pharmaceutical Science

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

71 Citations (Scopus)

Abstract

The hydration of o-ethynylbenzoic acid derivatives, such as ethyl o-ethynylbenzoate, o-ethynylbenzonitrile, and o-ethynylbenzamide, in sulfuric acid in the presence of mercuric sulfate, afforded 3-substituted isocoumarins. The palladium-catalyzed reaction of o-halobenzoic acid derivatives with terminal acetylenes to obtain the starting materials for the cyclization is also described.

Original language	English
Pages (from-to)	2754-2759
Number of pages	6
Journal	Chemical and Pharmaceutical Bulletin
Volume	34
Issue number	7
DOIs	https://doi.org/10.1248/cpb.34.2754
Publication status	Published - 1986 Jan 1

Keywords

acetylene
ethyl o-ethynylbenzoate
isocoumarin
mercuric sulfate
o-ethynylbenzamide
o-ethynylbenzonitrile
palladium-catalyzed reaction

ASJC Scopus subject areas

Chemistry(all)
Drug Discovery

Access to Document

10.1248/cpb.34.2754

Cite this

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title = "Condensed Heteroaromatic Ring Systems. VIII.1) Synthesis of 3-Substituted Isocoumarins from o-Halobenzoic Acid Derivatives",

abstract = "The hydration of o-ethynylbenzoic acid derivatives, such as ethyl o-ethynylbenzoate, o-ethynylbenzonitrile, and o-ethynylbenzamide, in sulfuric acid in the presence of mercuric sulfate, afforded 3-substituted isocoumarins. The palladium-catalyzed reaction of o-halobenzoic acid derivatives with terminal acetylenes to obtain the starting materials for the cyclization is also described.",

keywords = "acetylene, ethyl o-ethynylbenzoate, isocoumarin, mercuric sulfate, o-ethynylbenzamide, o-ethynylbenzonitrile, palladium-catalyzed reaction",

author = "Takao Sakamoto and Masayuki An-Naka and Yoshinori Kondo and Hiroshi Yamanaka",

year = "1986",

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doi = "10.1248/cpb.34.2754",

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TY - JOUR

T1 - Condensed Heteroaromatic Ring Systems. VIII.1) Synthesis of 3-Substituted Isocoumarins from o-Halobenzoic Acid Derivatives

AU - Sakamoto, Takao

AU - An-Naka, Masayuki

AU - Kondo, Yoshinori

AU - Yamanaka, Hiroshi

PY - 1986/1/1

Y1 - 1986/1/1

N2 - The hydration of o-ethynylbenzoic acid derivatives, such as ethyl o-ethynylbenzoate, o-ethynylbenzonitrile, and o-ethynylbenzamide, in sulfuric acid in the presence of mercuric sulfate, afforded 3-substituted isocoumarins. The palladium-catalyzed reaction of o-halobenzoic acid derivatives with terminal acetylenes to obtain the starting materials for the cyclization is also described.

AB - The hydration of o-ethynylbenzoic acid derivatives, such as ethyl o-ethynylbenzoate, o-ethynylbenzonitrile, and o-ethynylbenzamide, in sulfuric acid in the presence of mercuric sulfate, afforded 3-substituted isocoumarins. The palladium-catalyzed reaction of o-halobenzoic acid derivatives with terminal acetylenes to obtain the starting materials for the cyclization is also described.

KW - acetylene

KW - ethyl o-ethynylbenzoate

KW - isocoumarin

KW - mercuric sulfate

KW - o-ethynylbenzamide

KW - o-ethynylbenzonitrile

KW - palladium-catalyzed reaction

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DO - 10.1248/cpb.34.2754

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VL - 34

SP - 2754

EP - 2759

JO - Chemical and Pharmaceutical Bulletin

JF - Chemical and Pharmaceutical Bulletin

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