Palladium-Catalyzed Reactions of Terminal Acetylenes and Olefins with Halo-1,3-azoles

Takao Sakamoto; Hideo Nagata; Yoshinori Kondo; Masafumi Shiraiwa; Hiroshi Yamanaka

doi:10.1248/cpb.35.823

Palladium-Catalyzed Reactions of Terminal Acetylenes and Olefins with Halo-1,3-azoles

Takao Sakamoto, Hideo Nagata, Yoshinori Kondo, Masafumi Shiraiwa, Hiroshi Yamanaka

PHA - Molecular Pharmaceutical Science

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

45 Citations (Scopus)

Abstract

The palladium-catalyzed reactions of 4-bromo- and 5-bromothiazoles, as well as 4-bromo- and 5-bromooxazoles with terminal acetylenes gave ethynyl derivatives in 43—89% yields, whereas the reactions of 2-bromothiazoles and iodo-N-methylimidazoles afforded the products in poor yields. The reaction of the halo-1,3-azoles with terminal olefins was also examined.

Original language	English
Pages (from-to)	823-828
Number of pages	6
Journal	Chemical and Pharmaceutical Bulletin
Volume	35
Issue number	2
DOIs	https://doi.org/10.1248/cpb.35.823
Publication status	Published - 1987

Keywords

bromooxazole
bromothiazole
ethenyl-N-methylimidazole
ethenyl-oxazole
ethenylthiazole
ethynyl-N-methylimidazole
ethynyloxazole
ethynylthiazole
iodo-N-methyl-imidazole
palladium-catalyzed reaction

ASJC Scopus subject areas

Chemistry(all)
Drug Discovery

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10.1248/cpb.35.823

Cite this

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title = "Palladium-Catalyzed Reactions of Terminal Acetylenes and Olefins with Halo-1,3-azoles",

abstract = "The palladium-catalyzed reactions of 4-bromo- and 5-bromothiazoles, as well as 4-bromo- and 5-bromooxazoles with terminal acetylenes gave ethynyl derivatives in 43—89% yields, whereas the reactions of 2-bromothiazoles and iodo-N-methylimidazoles afforded the products in poor yields. The reaction of the halo-1,3-azoles with terminal olefins was also examined.",

keywords = "bromooxazole, bromothiazole, ethenyl-N-methylimidazole, ethenyl-oxazole, ethenylthiazole, ethynyl-N-methylimidazole, ethynyloxazole, ethynylthiazole, iodo-N-methyl-imidazole, palladium-catalyzed reaction",

author = "Takao Sakamoto and Hideo Nagata and Yoshinori Kondo and Masafumi Shiraiwa and Hiroshi Yamanaka",

year = "1987",

doi = "10.1248/cpb.35.823",

language = "English",

volume = "35",

pages = "823--828",

journal = "Chemical and Pharmaceutical Bulletin",

issn = "0009-2363",

publisher = "Pharmaceutical Society of Japan",

number = "2",

}

TY - JOUR

T1 - Palladium-Catalyzed Reactions of Terminal Acetylenes and Olefins with Halo-1,3-azoles

AU - Sakamoto, Takao

AU - Nagata, Hideo

AU - Kondo, Yoshinori

AU - Shiraiwa, Masafumi

AU - Yamanaka, Hiroshi

PY - 1987

Y1 - 1987

N2 - The palladium-catalyzed reactions of 4-bromo- and 5-bromothiazoles, as well as 4-bromo- and 5-bromooxazoles with terminal acetylenes gave ethynyl derivatives in 43—89% yields, whereas the reactions of 2-bromothiazoles and iodo-N-methylimidazoles afforded the products in poor yields. The reaction of the halo-1,3-azoles with terminal olefins was also examined.

AB - The palladium-catalyzed reactions of 4-bromo- and 5-bromothiazoles, as well as 4-bromo- and 5-bromooxazoles with terminal acetylenes gave ethynyl derivatives in 43—89% yields, whereas the reactions of 2-bromothiazoles and iodo-N-methylimidazoles afforded the products in poor yields. The reaction of the halo-1,3-azoles with terminal olefins was also examined.

KW - bromooxazole

KW - bromothiazole

KW - ethenyl-N-methylimidazole

KW - ethenyl-oxazole

KW - ethenylthiazole

KW - ethynyl-N-methylimidazole

KW - ethynyloxazole

KW - ethynylthiazole

KW - iodo-N-methyl-imidazole

KW - palladium-catalyzed reaction

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DO - 10.1248/cpb.35.823

M3 - Article

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VL - 35

SP - 823

EP - 828

JO - Chemical and Pharmaceutical Bulletin

JF - Chemical and Pharmaceutical Bulletin

SN - 0009-2363

IS - 2

ER -

Palladium-Catalyzed Reactions of Terminal Acetylenes and Olefins with Halo-1,3-azoles

Abstract

Keywords

ASJC Scopus subject areas

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