Facile Synthesis of Naphthothiophenone Derivatives and Anthradithiophenedione via Friedel-Crafts Acylation and Their Fundamental Properties

Koichi Mitsudo; Takashi Murakami; Takuya Shibasaki; Tomohiro Inada; Hiroki Mandai; Hiromi Ota; Seiji Suga

doi:10.1055/s-0035-1562470

Facile Synthesis of Naphthothiophenone Derivatives and Anthradithiophenedione via Friedel-Crafts Acylation and Their Fundamental Properties

Koichi Mitsudo, Takashi Murakami, Takuya Shibasaki, Tomohiro Inada, Hiroki Mandai, Hiromi Ota, Seiji Suga

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

4 Citations (Scopus)

Abstract

Facile synthetic methods for constructing naphthothiophenone and its π-extended derivatives were developed. Naphthothiophenone and anthradithiophenedione were synthesized by the S-acylation of thiol to form chlorothioformate and subsequent Friedel-Crafts acylation. A bromination reaction of naphthothiophenone and its application to Suzuki-Miyaura cross-coupling was also carried out. The fundamental physical properties of these compounds were also investigated.

Original language	English
Article number	st-2016-u0327-l
Pages (from-to)	2327-2332
Number of pages	6
Journal	Synlett
Volume	27
Issue number	16
DOIs	https://doi.org/10.1055/s-0035-1562470
Publication status	Published - Oct 4 2016

Keywords

acylation
anthradithiophenedione
cross-coupling
naphthothiophenone
thiophenone

ASJC Scopus subject areas

Organic Chemistry

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Facile Synthesis of Naphthothiophenone Derivatives and Anthradithiophenedione via Friedel-Crafts Acylation and Their Fundamental Properties. / Mitsudo, Koichi; Murakami, Takashi; Shibasaki, Takuya; Inada, Tomohiro; Mandai, Hiroki; Ota, Hiromi; Suga, Seiji.

In: Synlett, Vol. 27, No. 16, st-2016-u0327-l, 04.10.2016, p. 2327-2332.

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

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abstract = "Facile synthetic methods for constructing naphthothiophenone and its π-extended derivatives were developed. Naphthothiophenone and anthradithiophenedione were synthesized by the S-acylation of thiol to form chlorothioformate and subsequent Friedel-Crafts acylation. A bromination reaction of naphthothiophenone and its application to Suzuki-Miyaura cross-coupling was also carried out. The fundamental physical properties of these compounds were also investigated.",

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author = "Koichi Mitsudo and Takashi Murakami and Takuya Shibasaki and Tomohiro Inada and Hiroki Mandai and Hiromi Ota and Seiji Suga",

note = "Funding Information: We thank Prof. Yasushi Nishihara and Dr. Hiroki Mori (Okayama University) for their participation in fruitful discussions. We also thank Prof. Tetsuya Uchida, Mr. Fumiaki Iwaguro, and Mr. Makoto Nitta (Okayama University) for TG-DTA measurements. This work was supported in part by a Grant-in-Aid for Scientific Research (C) (No.25410042) from JSPS, Japan, and JST, ACT-C, Japan.",

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AU - Shibasaki, Takuya

AU - Inada, Tomohiro

AU - Mandai, Hiroki

AU - Ota, Hiromi

AU - Suga, Seiji

N1 - Funding Information: We thank Prof. Yasushi Nishihara and Dr. Hiroki Mori (Okayama University) for their participation in fruitful discussions. We also thank Prof. Tetsuya Uchida, Mr. Fumiaki Iwaguro, and Mr. Makoto Nitta (Okayama University) for TG-DTA measurements. This work was supported in part by a Grant-in-Aid for Scientific Research (C) (No.25410042) from JSPS, Japan, and JST, ACT-C, Japan.

PY - 2016/10/4

Y1 - 2016/10/4

N2 - Facile synthetic methods for constructing naphthothiophenone and its π-extended derivatives were developed. Naphthothiophenone and anthradithiophenedione were synthesized by the S-acylation of thiol to form chlorothioformate and subsequent Friedel-Crafts acylation. A bromination reaction of naphthothiophenone and its application to Suzuki-Miyaura cross-coupling was also carried out. The fundamental physical properties of these compounds were also investigated.

AB - Facile synthetic methods for constructing naphthothiophenone and its π-extended derivatives were developed. Naphthothiophenone and anthradithiophenedione were synthesized by the S-acylation of thiol to form chlorothioformate and subsequent Friedel-Crafts acylation. A bromination reaction of naphthothiophenone and its application to Suzuki-Miyaura cross-coupling was also carried out. The fundamental physical properties of these compounds were also investigated.

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KW - anthradithiophenedione

KW - cross-coupling

KW - naphthothiophenone

KW - thiophenone

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Facile Synthesis of Naphthothiophenone Derivatives and Anthradithiophenedione via Friedel-Crafts Acylation and Their Fundamental Properties

Abstract

Keywords

ASJC Scopus subject areas

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