Synlett 2016; 27(16): 2327-2332
DOI: 10.1055/s-0035-1562470
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© Georg Thieme Verlag Stuttgart · New York

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

Koichi Mitsudo*
a   Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan   Email: mitsudo@cc.okayama-u.ac.jp   Email: suga@cc.okayama-u.ac.jp
,
Takashi Murakami
a   Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan   Email: mitsudo@cc.okayama-u.ac.jp   Email: suga@cc.okayama-u.ac.jp
,
Takuya Shibasaki
a   Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan   Email: mitsudo@cc.okayama-u.ac.jp   Email: suga@cc.okayama-u.ac.jp
,
Tomohiro Inada
a   Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan   Email: mitsudo@cc.okayama-u.ac.jp   Email: suga@cc.okayama-u.ac.jp
,
Hiroki Mandai
a   Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan   Email: mitsudo@cc.okayama-u.ac.jp   Email: suga@cc.okayama-u.ac.jp
,
Hiromi Ota
b   Division of Instrumental Analysis, Department of Instrumental Analysis & Cryogenics, Advanced Research Center, Okayama University, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan
,
Seiji Suga*
a   Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan   Email: mitsudo@cc.okayama-u.ac.jp   Email: suga@cc.okayama-u.ac.jp
c   Research Center of New Functional Materials for Energy Production, Storage and Transport, Okayama University, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan
› Author Affiliations
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Publication History

Received: 08 May 2016

Accepted after revision: 14 June 2016

Publication Date:
19 July 2016 (online)


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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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