Superacid-catalyzed tandem Meyer–Schuster rearrangement/intramolecular hydroamination of o-anilinopropargyl alcohols for the synthesis of 2, 3-dihydro-4(1H)-quinolones. Issue 15 (2nd August 2016)

• Record Type: Journal Article
• Authors: Sun, Guofeng; Cheng, Fengkai; Tao, Ruiheng; Sun, Yuxing; Pan, Jinpeng; Zhu, Yaohua; Wang, Zhonghua; Wu, Fanhong; Yin, Yan
• Is Part Of: Synthetic communications. Volume 46:Issue 15(2016)
• Page Start: 1249
• Page End: 1256
• Publication Date: 2016-08-02
• Subjects: 2, 3-Dihydro-4(1H)-quinolones -- hydroamination reaction -- Meyer–Schuster rearrangement -- o-anilinopropargyl alcohols -- superacid; Organic compounds -- Synthesis -- Periodicals; Chemistry, Organic; Synthesis; 547.205
• DOI: 10.1080/00397911.2016.1196293
• Languages: English
• ISSNs: 0039-7911

Abstract

ABSTRACT: A TfOH-catalyzed synthesis of 2, 3-dihydro-4(1H)-quinolones from o -anilinopropargyl alcohols was developed. Studies of N -protecting groups and substituents in phenyl rings showed that diverse groups could be applied. By controlling the catalyst loading, o -anilinopropargyl alcohols underwent the expected transformation smoothly to produce N -protected or N -deprotected 2, 3-dihydro-4 (1H)-quinolones in good yields. This transformation probably involved a tandem Meyer–Schuster rearrangement/intramolecular hydroamination reaction process. GRAPHICAL ABSTRACT: