1-(3-Bromo-4-fluorophenyl)methanamine hydrochloride (1:1)
CAS Number:
202865-68-7
Molecular Formula:
C7H8BrClFN
Ring expansion and ring opening of 3-halooxindoles with N-alkoxycarbonyl-O-tosylhydroxylamines for divergent access to 4-aminoquinolin-2-ones and N-Cbz-N’-arylureas
Literature Information
Publication Date
2020-12-23
DOI
10.1039/D0QO01335H
Impact Factor
5.281
Authors
Wei-Cheng Yuan, Jian Zuo, Shu-Pei Yuan, Jian-Qiang Zhao, Zhen-Hua Wang, Yong You
View Original
Abstract
A divergent method for ring expansion and ring opening of 3-halooxindoles has been developed. Under mild base-mediated conditions, 3-halooxindoles generate indolones in situ, which then react smoothly with N-alkoxycarbonyl-O-tosylhydroxylamines to give 4-aminoquinolin-2-ones and N-Cbz-N′-arylureas in good to excellent yields via ring expansion and opening pathways, respectively. This protocol is characterized by easy availability of substrates, user-friendly reaction conditions, broad functional group tolerance, and a simple operation procedure.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
(E)-2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-2-ol
CAS Number:
581802-26-8
Molecular Formula:
C11H21BO3
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