A transition-metal-free, base-promoted annulation/ring-cleavage/ring-reconstruction cascade reaction: a facile access to N-protection free indole-indenones
Literature Information
Publication Date
2021-10-05
DOI
10.1039/D1QO01280K
Impact Factor
5.281
Authors
Na Luo, Zhen-Wei Sun, Xing-Xin Xu, Xiao-Qiang Hu, Feng-Cheng Jia
View Original
Abstract
A one-step, transition-metal-free, base-promoted cascade reaction of 2-halogenated arylglyoxals with 2-oxindoles is reported herein, which provides a straightforward approach to structurally diverse N-protection free indole-indenones in satisfactory yields. Control experiments indicated that the geminal bisindolin-2-one intermediate played a crucial role in the downstream annulation/ring-cleavage/ring-reconstruction reaction sequence. This novel reaction not only further enriches the reactivity of indolin-2-ones as the recursive enolate anion source, but also achieves thermal-induced α-arylation of oxindoles without a transition-metal catalyst.
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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
2-(2-Aminoethyl)-1H-isoindole-1,3(2H)-dione hydrochloride (1:1)
CAS Number:
30250-67-0
Molecular Formula:
C10H11ClN2O2
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