A palladium-catalyzed synthesis of isatins (1H-Indole-2,3-diones) from 1-(2-haloethynyl)-2-nitrobenzenes

Söderberg, Björn C.G.; Gorugantula, Sobha P.; Howerton, Chet R.; Petersen, Jeffrey L.; Dantale, Shubhada W.

doi:10.1016/j.tet.2009.06.098

Cited by 42 publications

(16 citation statements)

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“…While attempting to expand the range of substrates that can be cyclized in a palladium catalyzed reaction, Söderberg found that several palladium(II) complexes catalyze the cyclization of o‐ (haloethynyl)nitroarenes to the corresponding 1 H‐ indole‐2,3‐diones (isatins) (Scheme ) …”

Section: Miscellaneous Reactionsmentioning

confidence: 99%

Transition Metal Catalyzed Reductive Cyclization Reactions of Nitroarenes and Nitroalkenes

2019

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Nitroarenes are the entry point for the production of most nitrogen‐containing aromatic compounds. Thus, any transformation that leads directly from them to the final product allows saving one or more synthetic steps. This review deals with homogeneously catalyzed reactions leading to the formation of N‐heterocyclic compounds from nitroarenes or nitroalkenes in one pot. Reactions that lead to the intermediate formation of amines are not considered. Carbon monoxide is the most often employed reductant because it allows selective reactions, is cheap, and only produces CO2 as stoichiometric byproduct. However, the difficulty in handling pressurized CO has stimulated in recent years the development of CO‐surrogates, that is molecules able to liberate CO during the reaction. The use of phosphines and diols has also been developed in conjunction with molybdenum catalysts. The review focusses in more detail on the literature in the period 2006–2018, but reference to earlier work is made when necessary to put recent results in a more general context.

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Section: Miscellaneous Reactionsmentioning

confidence: 99%

Transition Metal Catalyzed Reductive Cyclization Reactions of Nitroarenes and Nitroalkenes

2019

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“…Our preliminary attempts to promote the cross‐coupling with the Pd/SPhos catalyst system delivered the expected product 2 , however, the yields were poor and the reaction mixtures were rather complex. We were aware of the potential of Pd‐catalyst to promote conversion of isatogens to isatins4c and so decided to establish whether or not this transformation could proceed smoothly in the absence of the Pd‐ligand system. Pleasingly, the addition of PhZnCl alone resulted in the formation of 2 in good yield.…”

Section: Resultsmentioning

confidence: 99%

Investigation of a Late‐Stage Derivatization Approach to Isatogens: Discovery of New Reaction Pathways

et al. 2015

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We have developed a new strategy for preparing 2‐substituted indolone N‐oxides (isatogens) by substitution reactions with aryl‐ and alkyl‐organometallic reagents. This approach allows a range of substituents to be incorporated at a late stage and complements existing methods that necessitate their early stage incorporation during substrate preparation. Further chemistry has been found to take place at the nitrone moiety; intramolecular dipolar cycloaddition provides access to angularly fused tricyclic heterocycles. More unusually however, these compounds are prone to further addition by organozinc reagents leading to 2,2‐disubstituted 3‐oxindole products.

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“…The method developed by Soderberg consists of catalytic heterocyclization of 1-(2-haloethynyl)-2-nitrobenzenes 33 or 34 and leads to the formation of 2-iodo(bromo)isatogens 35, which further, in refluxing acetone, convert into the corresponding aryl-substituted isatins 2 with moderate to high yields (Scheme 23). 49,50 Ilangovan and co-workers have described an iodination-Kornblum oxidation-nucleophilic addition sequence for the synthesis of diversely substituted isatins 2 from oaminostyrenes 36 or o-aminophenylacetylenes 37 (Scheme 24). 51…”

Section: Miscellaneousmentioning

confidence: 99%

Advances in the Synthesis of Isatins: A Survey of the Last Decade

Богданов

Миронов

2018

Synthesis

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Isatin derivatives are widely used in organic synthesis, in medicinal chemistry and in the chemistry of materials. This report summarizes modern trends in the synthesis of substituted indolin-2,3-diones covering the literature from 2007 to 2017. Studies on the influence of the structure of substituents in the initial substrates on the formation of the heterocyclic isatin system and the yields of the target compounds are also discussed.1 Introduction2 Oxidation of Indole Derivatives3 Cyclization of o-Aminoacetophenones4 Cyclization of N-Acylanilines5 Miscellaneous6 Conclusion

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A palladium-catalyzed synthesis of isatins (1H-Indole-2,3-diones) from 1-(2-haloethynyl)-2-nitrobenzenes

Cited by 42 publications

References 41 publications

Transition Metal Catalyzed Reductive Cyclization Reactions of Nitroarenes and Nitroalkenes

Transition Metal Catalyzed Reductive Cyclization Reactions of Nitroarenes and Nitroalkenes

Investigation of a Late‐Stage Derivatization Approach to Isatogens: Discovery of New Reaction Pathways

Advances in the Synthesis of Isatins: A Survey of the Last Decade

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A palladium-catalyzed synthesis of isatins (1H-Indole-2,3-diones) from 1-(2-haloethynyl)-2-nitrobenzenes

Cited by 42 publications

References 41 publications

Transition Metal Catalyzed Reductive Cyclization Reactions of Nitroarenes and Nitroalkenes

Transition Metal Catalyzed Reductive Cyclization Reactions of Nitroarenes and Nitroalkenes

Investigation of a Late‐Stage Derivatiza­tion Approach to Isatogens: Discovery of New Reaction Pathways

Advances in the Synthesis of Isatins: A Survey of the Last Decade

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Investigation of a Late‐Stage Derivatization Approach to Isatogens: Discovery of New Reaction Pathways