2016
DOI: 10.1002/ange.201607177
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Transition‐Metal‐Free Synthesis of N‐Hydroxy Oxindoles by an Aza‐Nazarov‐Type Reaction Involving Azaoxyallyl Cations

Abstract: An ovel transition-metal-free method to construct N-hydroxy oxindoles by an aza-Nazarov-type reaction involving azaoxyallyl cation intermediates is described. Avariety of functional groups were tolerated under the weak basic reaction conditions and at room temperature.Aone-pot process was also developed to make the reaction even more practical. This method provides alternative access to oxindoles and their biologically active derivatives.

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Cited by 10 publications
(3 citation statements)
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“…Although α-bromoanilides are one of the most commonly employed precursors for oxindole synthesis via intramolecular cyclization, [9][10][11][12][13] we also explored the possibility of using the corresponding chloroanilides or iodoanilides as the substrate for the reported reaction (Scheme 2). Satisfyingly, oxindole 2a was synthesized in high yields when the chloro-or iodoanalogue of 1a was subjected to the optimized conditions.…”
Section: Resultsmentioning
confidence: 99%
See 1 more Smart Citation
“…Although α-bromoanilides are one of the most commonly employed precursors for oxindole synthesis via intramolecular cyclization, [9][10][11][12][13] we also explored the possibility of using the corresponding chloroanilides or iodoanilides as the substrate for the reported reaction (Scheme 2). Satisfyingly, oxindole 2a was synthesized in high yields when the chloro-or iodoanalogue of 1a was subjected to the optimized conditions.…”
Section: Resultsmentioning
confidence: 99%
“…Recently, Liao and coworkers reported the transition-metal-free synthesis of N-hydroxy oxindoles via an aza-Nazarov-type reaction. 13 During the last decade, transition-metal-free reactions have emerged as important methods for the formation of C-C bonds. 14 Very recently, we developed a NHC-catalyzed route for the transformation of α-bromoanilides into oxindoles, which was believed to proceed via a single electron transfer (SET) process (Scheme 1b).…”
Section: Introductionmentioning
confidence: 99%
“…1 Although the oxindole scaffold widely exists in plant-based alkaloids, some specially designed derivatives rely on artificial synthesis. 2 Besides direct derivatization from indoles or isatins, 3 over the last few decades, several synthetic strategies have been developed from non-indole precursors bearing different functionalities and thus via diverse pathways, such as the Friedel-Crafts reaction, 4 the aza-Nazarov type reaction, 5 transition metal catalyzed cyclization, [6][7][8][9][10][11] radical cyclization, 11,12 electrochemical crosscoupling reaction, 13 etc. 14 Given their profound importance in both academia and pharma industry, the development of novel efficient synthetic methods for the construction of various oxindole derivatives has attracted much attention, and an endless stream of novel structures and new bonding modes have been emerging.…”
Section: Introductionmentioning
confidence: 99%