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Synthesis of Benzo[c]azepine-1,3(2H)-diones via C−H Alkylation/Cyclization with α,β-Unsaturated Acyl Fluorides

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Title: Synthesis of Benzo[c]azepine-1,3(2H)-diones via C−H Alkylation/Cyclization with α,β-Unsaturated Acyl Fluorides
Authors: Hosoi, Satoko Browse this author
Hirata, Yuki Browse this author
Kurihara, Takumaru Browse this author
Kojima, Masahiro Browse this author →KAKEN DB
Yoshino, Tatsuhiko Browse this author →KAKEN DB
Matsunaga, Shigeki Browse this author →KAKEN DB
Keywords: benzo[c]azepine-1,3(2H)-dione
C-H activation
α,β-unsaturated acyl fluoride
hydroxamate imide
Issue Date: 17-May-2023
Publisher: Wiley-Blackwell
Journal Title: Asian journal of organic chemistry
Volume: 12
Issue: 8
Start Page: e202300218
Publisher DOI: 10.1002/ajoc.202300218
Abstract: Transition-metal-catalyzed directed C-H functionalization reactions are a powerful method to construct N-heterocycles. However, compared to the formation of five- and six-membered rings, that of seven-membered rings has been much less explored. Here, the synthesis of benzo[c]azepine-1,3(2H)-diones is described, which are benzene-fused seven-membered imides, from hydroxamates and α,β-unsaturated acyl fluorides via C-H activation using a Cp*Rh(III) catalyst. Under mild reaction conditions, this reaction affords benzo[c]azepine-1,3(2H)-diones that bear a substituent at the 5-position.
Rights: This is the pre-peer reviewed version of the following article: https://onlinelibrary.wiley.com/doi/10.1002/ajoc.202300218, which has been published in final form at 10.1002/ajoc.202300218. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.
Type: article (author version)
URI: http://hdl.handle.net/2115/92583
Appears in Collections:薬学研究院 (Faculty of Pharmaceutical Sciences) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 吉野 達彦

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