[Bis‐(trifluoroacetoxy)iodo]benzene‐Mediated Oxidative Direct Amination C–N Bond Formation: Synthesis of 1<i>H</i>‐Indazoles

Zhang, Zhiguo; Huang, Yuanyuan; Huang, Guoqing; Zhang, Guisheng; Li, Qingfeng

doi:10.1002/jhet.2839

Cited by 25 publications

(12 citation statements)

References 64 publications

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“…We recently established two new reliable, efficient, and green methods for the synthesis of 1 H -indazoles and spirocyclopropane quinolinediones under mild conditions. Notably, both of these methods required the presence of a hypervalent iodine reagent and proceeded via an intramolecular oxidative C–N bond forming reaction . Encouraged by these results, we became interested in expanding the scope of organoiodine reagents in organic synthesis.…”

Section: Introductionsupporting

confidence: 75%

Selective Cleavage of Inert Aryl C–N Bonds in N-Aryl Amides

et al. 2018

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A highly selective, IBX-promoted reaction has been developed for the oxidative cleavage of inert C(aryl)-N bonds on secondary amides while leaving the C(carbonyl)-N bond unchanged. This metal-free reaction proceeds under mild conditions (HFIP/HO, 25 °C), providing facile access to various useful primary amides, some of which would be otherwise unattainable using conventional aminolysis and hydrolysis approaches.

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Section: Introductionsupporting

confidence: 75%

Selective Cleavage of Inert Aryl C–N Bonds in N-Aryl Amides

et al. 2018

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“…Chang et al [ 16 ] treated diaryl and tert -butyl aryl ketone hydrazones 8 with iodine in the presence of potassium iodide and sodium acetate obtaining 1 H -indazoles 9 via direct aryl C-H amination, as shown in Scheme 2 . The synthesis of 1 H -indazoles 11 from arylhydrazones 10 through direct aryl C-H amination using [bis-(trifluoroacetoxy)iodo]benzene (PIFA) as an oxidant was described by Zhang et al ( Scheme 3 ) [ 17 ]. The reaction displayed good functional group compatibility and provided the corresponding compounds in good yields.…”

Section: Synthesis Route For Indazole Derivativesmentioning

confidence: 99%

Recent Advances in Indazole-Containing Derivatives: Synthesis and Biological Perspectives

2018

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Indazole-containing derivatives represent one of the most important heterocycles in drug molecules. Diversely substituted indazole derivatives bear a variety of functional groups and display versatile biological activities; hence, they have gained considerable attention in the field of medicinal chemistry. This review aims to summarize the recent advances in various methods for the synthesis of indazole derivatives. The current developments in the biological activities of indazole-based compounds are also presented.

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“…The liberated iodobenzene is reoxidized to PhI(III) by oxone. Recently, similar strategy was developed for the synthesis of substituted 1 H ‐indazoles 153 from readily available arylhydrazones 152 using PIFA ( 2 ) by Zhang and co‐authors (Scheme b) …”

Section: Intramolecular Oxidative C(sp2)‐n Bond Formationmentioning

confidence: 99%

Recent Advances in Intramolecular Metal‐Free Oxidative C–H Bond Aminations Using Hypervalent Iodine(III) Reagents

et al. 2019

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Hypervalent iodine chemistry is a rapidly growing area of research with tremendous impact on synthetic chemistry in the past years. A rich and diverse chemistry is now available for reactions using hypervalent iodine reagents, as metal‐free, ecofriendly reagents and the advent of new reactions will be of large benefit to researchers working in the area of selective synthesis. In this review article, we emphasize the usage of hypervalent iodine(III) reagents for metal‐free intramolecular oxidative C–N bond formation/annulation to synthesize wide range of N‐heterocycles in organic synthesis. The functionalization of C–H bonds through the involvement of sp‐, sp2‐, and sp3‐hybridized carbon atoms for cyclizations is discussed in detail.

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[Bis‐(trifluoroacetoxy)iodo]benzene‐Mediated Oxidative Direct Amination C–N Bond Formation: Synthesis of 1H‐Indazoles

Cited by 25 publications

References 64 publications

Selective Cleavage of Inert Aryl C–N Bonds in N-Aryl Amides

Selective Cleavage of Inert Aryl C–N Bonds in N-Aryl Amides

Recent Advances in Indazole-Containing Derivatives: Synthesis and Biological Perspectives

Recent Advances in Intramolecular Metal‐Free Oxidative C–H Bond Aminations Using Hypervalent Iodine(III) Reagents

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