Synthesis of Iodine‐Substituted Quinolines, Quinolinium Salts, and Isoquinolinium Salts via a Three‐Component Tandem Reaction of Aryl Azides, Propargylic Alcohols, and Iodine. Issue 1 (1st December 2016)

• Record Type: Journal Article
• Authors: Wu, Yunjun; Shao, Min; Feng, Zhijun; Gu, Xiaoxia; Hong, Yi; Cui, Qiaoyu; Ren, Lianbing; Wang, Shaoyin
• Is Part Of: Asian journal of organic chemistry. Volume 6:Issue 1(2017)
• Page Start: 76
• Page End: 82
• Publication Date: 2016-12-01
• Subjects: azides -- Friedel–Crafts reaction -- heterocycles -- multicomponent reactions -- propargylic alcohols; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201600503
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: 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. Abstract : Reactions of Propargylic Alcohols : A concise, metal‐free, one‐pot method has been developed for the facile synthesis of functionalized quinolinium salts and quinolines from readily available aryl azides, propargylic alcohols and iodine.