Synthesis of Iodine-Substituted Quinolines, Quinolinium Salts, and Isoquinolinium Salts via a Three-Component Tandem Reaction of Aryl Azides, Propargylic Alcohols, and Iodine
详细信息 查看全文
- 作者：Dr. Yunjun Wu ; Min Shao ; Dr. Zhijun Feng ; Dr. Xiaoxia Gu ; Yi Hong ; Qiaoyu Cui ; Dr. Lianbing Ren and Dr. Shaoyin Wang
- 刊名：Asian Journal of Organic Chemistry
- 出版年：2017
- 出版时间：January 2017
- 年：2017
- 卷：6
- 期：1
- 页码：76-82
- 全文大小：898K
- ISSN：2193-5815
文摘
An efficient three-component tandem reaction of aryl azides, propargylic alcohols, and iodine has been developed. The products of the reaction hinge on the type of the propargylic alcohols: for tertiary alcohols, the reaction proceeded via a cascade Friedel–Crafts-type reaction/electrophilic cyclization/1,2-aryl migratory shift sequence to provide 3-iodoquinolinium salt products, while in the case of secondary alcohols, 3-iodoquinoline products could be obtained. For aryl azides with certain substituents, this method gave novel isoquinoline skeletons.