An improved synthesis of isonitrosoacetanilides

Rewcastle, Gordon W.; Sutherland, Hamish S.; Weir, Claudette A.; Blackburn, Adrian G.; Denny, William A.

doi:10.1016/j.tetlet.2005.10.046

Cited by 18 publications

(12 citation statements)

References 16 publications

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“…However, the treatment of 3-aminothiophene with conventional reagents that are suitable for the synthesis of isatin, such as oxalyl chloride and trichloroacetic chloride, under various conditions failed to afford the desired product, which may be attributed to the highly reactive electron-rich thiophene. Fortunately, we finally found that by treating compound 1 with 2-chloro-2-oxoethane-1,1-diyl diacetate with the sequential addition of hydroxylamine using Rewcastle’s method, the corresponding oxime, 2 , could be obtained in decent yield, 19 as shown in Scheme 2. This is the key step toward thieno-isatin synthesis.…”

Section: Resultsmentioning

confidence: 99%

Efficient Route toward N-Unsubstituted Thienoisoindigo Suitable for Side-Chain Engineering

Zhang

Cai

et al. 2017

ACS Omega

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Section: Resultsmentioning

confidence: 99%

Efficient Route toward N-Unsubstituted Thienoisoindigo Suitable for Side-Chain Engineering

Zhang

Cai

et al. 2017

ACS Omega

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“…The synthesis of roelactamine commenced with the sequential reaction of piperonal ( 72 ) with methylamine, the Grignard reagent 75 , and diacetoxyacetyl chloride ( 76 ), which was easily prepared in gram quantities from glyoxylic acid,47 to give amide 73 (Scheme 18). When 73 was simply treated with HCl and MeOH, roelactamine ( 74 ) was formed and isolated in good overall yield from 72 .…”

Section: Resultsmentioning

confidence: 99%

“…A solution of the Grignard reagent ( 75 ) thus prepared (0.4 M in THF, 3.5 mL, 1.40 mmol) was added to the mixture of the imine, and the reaction was heated under reflux for 20 h. The mixture was cooled to -78 °C, and diacetoxyacetyl chloride ( 76 )47 (358 mg, 1.83 mmol) was added. The reaction was stirred for 2.5 h at -78 °C.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of diverse heterocyclic scaffolds via tandem additions to imine derivatives and ring-forming reactions

2009

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A novel strategy has been developed for the efficient syntheses of diverse arrays of heterocyclic compounds. The key elements of the approach comprise a Mannich-type, multicomponent coupling reaction in which functionalized amines, aromatic aldehydes, acylating agents, and π-and organometallic nucleophiles are combined to generate intermediates that are then further transformed into diverse heterocyclic scaffolds via a variety of cyclization manifolds. Significantly, many of these scaffolds bear functionality that may be exploited by further manipulation to create diverse collections of compounds having substructures found in biologically active natural products and clinically useful drugs. The practical utility of this strategy was exemplified by its application to the first, and extraordinarily concise synthesis of the isopavine alkaloid roelactamine.

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“…Quinolines, acridines, and indophenazines have all been made from the isatin derivatives produced by this reaction [30,31]. The Sandmeyer method for synthesis of isonitrosoacetanilides is less effective with aniline derivatives that have low solubility in aqueous sodium sulphate medium, but it also fails to work well with anilines that have electron-rich ortho [32].…”

Section: Synthesis Of Isatin 51 the Sandmeyer Isatin Synthesismentioning

confidence: 99%

A Review on Isatin and Its Derivatives: Synthesis, Reactions and Applications

Gandhi¹,

Burande²,

Charde³

et al. 2021

JASR

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Isatin, also known as 1H-Indole-2, 3-Dione, is an eight-carbon containing endogenous compound found in nature. Erdmann and Laurent synthesized isatin in 1840, before it was discovered in nature. It is versatile and distributed in tissues and body fluids. Isatins have also been detected in mammalian tissue, and their function as a biochemical process modulator has been the focus of many debates. The isatin moiety also shows some important chemical reactions such as oxidation, N-Acylation, Friedel-Crafts reaction, N-Halogenation, etc. Antitumor, antimicrobial, anti-inflammatory, anticonvulsant, antiviral, anti-HIV, antioxidant, and CNS depressant functions are all possessed by simple isatin nucleus. Substituted derivatives of this compound also have these properties. The isatin derivatives are effective inhibitors of the urease and α-glucosidase enzymes. This review provides a brief overview on the some commonly used procedures to synthesize the isatin moiety and its derivatives, its physical properties, reactions and biological activities.

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An improved synthesis of isonitrosoacetanilides

Cited by 18 publications

References 16 publications

Efficient Route toward N-Unsubstituted Thienoisoindigo Suitable for Side-Chain Engineering

Efficient Route toward N-Unsubstituted Thienoisoindigo Suitable for Side-Chain Engineering

Synthesis of diverse heterocyclic scaffolds via tandem additions to imine derivatives and ring-forming reactions

A Review on Isatin and Its Derivatives: Synthesis, Reactions and Applications

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