Substituent Effect of Imino-<i>O</i>-arenesulfonates, a Coupling Partner in Suzuki–Miyaura Reaction for Substitution of the Pyrazine Ring: A Study for the Synthesis of Coelenterazine Analogs

• Makarasen Arthit

  Graduate School of Bioagricultural Sciences, Nagoya University

• Kuse Masaki

  Institute of Material Science, Nagoya University

• Nishikawa Toshio

  Graduate School of Bioagricultural Sciences, Nagoya University

• Isobe Minoru

  Graduate School of Bioagricultural Sciences, Nagoya University Institute for Advanced Research, Nagoya University

書誌事項

タイトル別名

• Substituent Effect of Imino-O-arenesulfonates, a Coupling Partner in Suzuki-Miyaura Reaction for Substitution of the Pyrazine Ring: A Study for the Synthesis of Coelenterazine Analogs

抄録

Amino(aryl)pyrazines, a key intermediate in the synthesis of coelenterazine and its analogs, can be prepared in excellent yields by utilizing imino-O-tosylates in the Suzuki–Miyaura reaction. These imino-O-tosylates serve as a substitute for the corresponding imino-O-triflates, which are sometimes too unstable to be stored during the optimization of the reaction conditions. Aryltrifluoroborates, a coupling partner, worked well when arylboronic acids or arylboronate esters were less reactive. Aryltrifluoroborates also worked well when containing an electron-donating group attached to the aromatic ring. The study of the substituent effect of imino-O-arenesulfonates demonstrated a major difference in the rate of the reactions when changing from electron-donating groups to electron-withdrawing groups at the para position of arenesulfonates. Imino-O-arenesulfonate containing a para-bromo substituent only gave the desired coupling product leaving the para substituent of arenesulfonate untouched.

収録刊行物

• Bulletin of the Chemical Society of Japan

  Bulletin of the Chemical Society of Japan 82 (7), 870-878, 2009

  公益社団法人 日本化学会

キーワード

• General Chemistry

詳細情報

• CRID: 1390282679118352000
• NII論文ID: 130004152630
• NII論文ID: 10025126416
• NII書誌ID: AA00580132
• DOI: 10.1246/bcsj.82.870
• ISSN: 13480634
• ISSN: 00092673
• NDL書誌ID: 10277050
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I10277050
• Web Site: https://academic.oup.com/bcsj/article-pdf/82/7/870/56270940/bcsj.82.870.pdf
• 本文言語コード: en
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