Thiazolobenzyne: A versatile intermediate for multisubstituted benzothiazoles

Suguru Yoshida; Takahisa Yano; Yoshitake Nishiyama; Yoshihiro Misawa; Masakazu Kondo; Takeshi Matsushita; Kazunobu Igawa; Katsuhiko Tomooka; Takamitsu Hosoya

doi:10.1039/c6cc05112j

Thiazolobenzyne: A versatile intermediate for multisubstituted benzothiazoles

Suguru Yoshida, Takahisa Yano, Yoshitake Nishiyama, Yoshihiro Misawa, Masakazu Kondo, Takeshi Matsushita, Kazunobu Igawa, Katsuhiko Tomooka, Takamitsu Hosoya

Department of Applied Molecular Chemistry

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

27 Citations (Scopus)

Abstract

Thiazolobenzyne, which is a benzyne species fused with a thiazole ring, was efficiently generated via an iodine-magnesium exchange reaction of an ortho-iodoaryl triflate-type precursor using a trimethylsilylmethyl Grignard reagent as an activator. A wide range of arynophiles reacted efficiently with the thiazolobenzynes generated by this method to afford various multisubstituted benzothiazoles.

Original language	English
Pages (from-to)	11199-11202
Number of pages	4
Journal	Chemical Communications
Volume	52
Issue number	75
DOIs	https://doi.org/10.1039/c6cc05112j
Publication status	Published - 2016

All Science Journal Classification (ASJC) codes

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
Chemistry(all)
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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10.1039/c6cc05112j

Cite this

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title = "Thiazolobenzyne: A versatile intermediate for multisubstituted benzothiazoles",

abstract = "Thiazolobenzyne, which is a benzyne species fused with a thiazole ring, was efficiently generated via an iodine-magnesium exchange reaction of an ortho-iodoaryl triflate-type precursor using a trimethylsilylmethyl Grignard reagent as an activator. A wide range of arynophiles reacted efficiently with the thiazolobenzynes generated by this method to afford various multisubstituted benzothiazoles.",

author = "Suguru Yoshida and Takahisa Yano and Yoshitake Nishiyama and Yoshihiro Misawa and Masakazu Kondo and Takeshi Matsushita and Kazunobu Igawa and Katsuhiko Tomooka and Takamitsu Hosoya",

note = "Funding Information: This work was supported by the Platform for Drug Discovery, Informatics, and Structural Life Science from MEXT and AMED, Japan; CREST from JST and AMED, Japan; JSPS KAKENHI Grant Numbers 15H03118 (B; T. H.), 16H01133 (Middle Molecular Strategy; T. H.) and 26350971 (C; S. Y.); and the Cooperative Research Program of Network Joint Research Center for Materials and Devices. Publisher Copyright: {\textcopyright} 2016 The Royal Society of Chemistry.",

year = "2016",

doi = "10.1039/c6cc05112j",

language = "English",

volume = "52",

pages = "11199--11202",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "75",

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T1 - Thiazolobenzyne

T2 - A versatile intermediate for multisubstituted benzothiazoles

AU - Yoshida, Suguru

AU - Yano, Takahisa

AU - Nishiyama, Yoshitake

AU - Misawa, Yoshihiro

AU - Kondo, Masakazu

AU - Matsushita, Takeshi

AU - Igawa, Kazunobu

AU - Tomooka, Katsuhiko

AU - Hosoya, Takamitsu

N1 - Funding Information: This work was supported by the Platform for Drug Discovery, Informatics, and Structural Life Science from MEXT and AMED, Japan; CREST from JST and AMED, Japan; JSPS KAKENHI Grant Numbers 15H03118 (B; T. H.), 16H01133 (Middle Molecular Strategy; T. H.) and 26350971 (C; S. Y.); and the Cooperative Research Program of Network Joint Research Center for Materials and Devices. Publisher Copyright: © 2016 The Royal Society of Chemistry.

PY - 2016

Y1 - 2016

N2 - Thiazolobenzyne, which is a benzyne species fused with a thiazole ring, was efficiently generated via an iodine-magnesium exchange reaction of an ortho-iodoaryl triflate-type precursor using a trimethylsilylmethyl Grignard reagent as an activator. A wide range of arynophiles reacted efficiently with the thiazolobenzynes generated by this method to afford various multisubstituted benzothiazoles.

AB - Thiazolobenzyne, which is a benzyne species fused with a thiazole ring, was efficiently generated via an iodine-magnesium exchange reaction of an ortho-iodoaryl triflate-type precursor using a trimethylsilylmethyl Grignard reagent as an activator. A wide range of arynophiles reacted efficiently with the thiazolobenzynes generated by this method to afford various multisubstituted benzothiazoles.

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JF - Chemical Communications

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IS - 75

ER -

Thiazolobenzyne: A versatile intermediate for multisubstituted benzothiazoles

Abstract

All Science Journal Classification (ASJC) codes

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