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タイトル: | Gold(I)-Catalyzed Cascade Cyclization of Anilines with Diynes: Controllable Formation of Eight-Membered Ring-Fused Indoles and Propellane-Type Indolines |
著者: | Yamaguchi, Ayuta Inuki, Shinsuke https://orcid.org/0000-0002-7525-1280 (unconfirmed) Tokimizu, Yusuke Oishi, Shinya Ohno, Hiroaki https://orcid.org/0000-0002-3246-4809 (unconfirmed) |
著者名の別形: | 山口, 亞由太 井貫, 晋輔 大石, 真也 大野, 浩章 |
発行日: | 21-Feb-2020 |
出版者: | NLM (Medline) |
誌名: | The Journal of organic chemistry |
巻: | 85 |
号: | 4 |
開始ページ: | 2543 |
終了ページ: | 2559 |
抄録: | Heterocycle-fused indoles or indolines are distributed widely in a variety of natural products, bioactive agents, and pharmaceuticals. Herein, we describe the development of gold-catalyzed cascade reactions of anilines with diynes to form eight-membered ring-fused indoles and propellane-type indolines, both of which proceed through an intramolecular 5-endo-dig hydroamination followed by an 8-endo-dig cycloisomerization. Controllable formation of eight-membered ring-fused indoles and propellane-type indolines was achieved through selection of the ligands and/or solvents. Protic solvents such as alcohols or IPr ligand favored the formation of eight-membered ring-fused indoles, whereas the use of Buchwald’s type ligands and/or nonpolar solvents gave propellane-type indoline predominantly. This reaction provides rapid access to two types of fused nitrogen heterocycles from simple aniline derivatives. |
著作権等: | This document is the Accepted Manuscript version of a Published Work that appeared in final form in The Journal of organic chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.joc.9b03256. The full-text file will be made open to the public on 8 January 2021 in accordance with publisher's 'Terms and Conditions for Self-Archiving'. This is not the published version. Please cite only the published version. この論文は出版社版でありません。引用の際には出版社版をご確認ご利用ください。 |
URI: | http://hdl.handle.net/2433/246557 |
DOI(出版社版): | 10.1021/acs.joc.9b03256 |
PubMed ID: | 31913037 |
出現コレクション: | 学術雑誌掲載論文等 |
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