Metal‐Free Oxidative C–H Amidation of N,N′‐Diarylureas with PhI(OAc)2: Synthesis of Benzimidazol‐2‐one Derivatives

Yu, Jipan; Gao, Cunxu; Song, Ziqi; Yang, Haijun; Fu, Hua

doi:10.1002/ejoc.201500726

Cited by 27 publications

(10 citation statements)

References 91 publications

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“…The carbonylation reaction of benzene-1,2-diamines requires the use of phosgene, triphosgene, or carbonyl diimidazole. 3 To avoid the use of such hazardous chemicals, alternative procedures using transition metals (palladium 4 and copper 5 )-catalyzed intramolecular 3 or intermolecular 4 cyclization or C–H oxidation 6 reactions were developed. Some of the interesting interconversions of heterocyclic rings for the synthesis of benzimidazol-2-ones are also reported.…”

Section: Resultsmentioning

confidence: 99%

Route to Benzimidazol-2-ones via Decarbonylative Ring Contraction of Quinoxalinediones: Application to the Synthesis of Flibanserin, A Drug for Treating Hypoactive Sexual Desire Disorder in Women and Marine Natural Product Hunanamycin Analogue

et al. 2017

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A simple and practical method to access a variety of benzimidazol-2-ones is reported here. A series of N-alkyl-substituted benzimidazol-2-ones were synthesized by decarbonylative ring contraction starting from corresponding quinoxalinediones for the first time. The utility of the method has been demonstrated by synthesizing recently approved controversial drug flibanserin (Addyi) and a urea analogue of marine antibiotic natural product hunanamycin-A.

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Section: Resultsmentioning

confidence: 99%

Route to Benzimidazol-2-ones via Decarbonylative Ring Contraction of Quinoxalinediones: Application to the Synthesis of Flibanserin, A Drug for Treating Hypoactive Sexual Desire Disorder in Women and Marine Natural Product Hunanamycin Analogue

et al. 2017

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“…(Scheme a) . Further, this same methodology was extended by Fu group to N , N′ ‐Diarylureas 73 with PIDA ( 1 ) oxidant, Cs 2 CO 3 as additive in HFIP solvent to obtain benzimidazol‐2‐one derivatives 74 in moderate to good yields (Scheme b) …”

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

confidence: 98%

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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“…In 2015, Fu et al. discovered the PIDA‐mediated oxidative C−H amination for the preparation of benzimidazol‐2‐ones 77 from readily available N , N′ ‐diarylureas 76 (Figure b) …”

Section: C−n Bond Formation Reactionsmentioning

confidence: 99%

Nitrenium Ions from Amine‐Iodine(III) Combinations

et al. 2019

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Hypervalent iodine compounds are known for their extensive use as potentialo xidants in organic synthesis.I ns pite of the similar reactivity with transitionm etals,h ypervalent iodine reagents are more preferred because of their environmental sustainability.A mong several types of hypervalent iodine reagents,t rivalent organoiodine(III) reagents are highly popular due to their easy accessibility,s tability and controlled oxidizing reactivity.A lso, iodine(III) reagents are commerciallya vailable andi nexpensive. Amines and amidesr eact with iodine(III) oxidants in some specificw ay to provide ad ivalent electrophilic ionic species known as an itrenium ion. Depending on the nature and stability of the nitrenium ion, numerous oxidative transformations to generate valuable functional molecules have been reported.T his review encompassesd iscussionsa bout hypervalent organo iodine(III)-enabled organic transformationsw ith the involvemento fanitrenium ion as an intermediate. Figure1.Ionic electrophilic speciesw ith 6v alance electrons.

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Metal‐Free Oxidative C–H Amidation of N,N′‐Diarylureas with PhI(OAc)₂: Synthesis of Benzimidazol‐2‐one Derivatives

Cited by 27 publications

References 91 publications

Route to Benzimidazol-2-ones via Decarbonylative Ring Contraction of Quinoxalinediones: Application to the Synthesis of Flibanserin, A Drug for Treating Hypoactive Sexual Desire Disorder in Women and Marine Natural Product Hunanamycin Analogue

Route to Benzimidazol-2-ones via Decarbonylative Ring Contraction of Quinoxalinediones: Application to the Synthesis of Flibanserin, A Drug for Treating Hypoactive Sexual Desire Disorder in Women and Marine Natural Product Hunanamycin Analogue

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

Nitrenium Ions from Amine‐Iodine(III) Combinations

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