Cascade Formation of C<sub>3</sub>‐Unsymmetric Spirooxindoles via PhI(OAc)<sub>2</sub>‐Mediated Oxidative C−C/C−N Bond Formation

Sun, Jiyun; Li, Guangchen; Zhang, Guangtao; Cong, Ying; An, Xuechan; Zhang‐Negrerie, Daisy; Du, Yunfei

doi:10.1002/adsc.201800314

Cited by 13 publications

(6 citation statements)

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“…It is worth noting that the presence of a strong electron‐withdrawing nitro group was also applicable to the method (40 % yield) ( Scheme 5). [91] Later, similar results were obtained by oxidizing compound 14b (R 2 =OMe) under the action of PIDA [92] …”

Section: Synthesis Of Spiroheterocycles From Arylamides Of Carboxylicsupporting

confidence: 52%

“…[91] Later, similar results were obtained by oxidizing compound 14b (R 2 = OMe) under the action of PIDA. [92] The spiroheterocyclic products were obtained in the diastereoselective oxidative cascade cyclization reaction of N-(2-allylaminophenyl)dienoic acid amides 16 under the action of palladium acetate in the presence of pyridine, substituted quinoline, acridine or isoquinoline. As a result of these transformations, a mixture of pyrrolo[1,2-a]indoles 17, 18 spiro-fused with cycloalkenes is formed.…”

Section: Synthesis Of Spiroheterocycles From Arylamides Of Carboxylicmentioning

confidence: 99%

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Advances in the Synthesis of Benzo‐Fused Spiro Nitrogen Heterocycles: New Approaches and Modification of Old Strategies

Гатауллин

2020

Helvetica Chimica Acta

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The review covers the results of studies published in the literature on the synthesis of spiro-linked heterocycles of the indole, quinoline, benzoxazine, benzothiazine, indenoquinoxaline, pyridopyrimidine, and acridine series. Possible approaches to the synthesis of spirocycles through a sequence of well-known Knoevenagel, Michael reactions, deamination cyclization of 1,2-dicarbonyl, CH-acid compounds, direct cycloaddition of activated olefins to isatins, 3-alkylideneindoles, 2-oxindoles, in situ generated azomethine ylides, indenoquinoxalines are analyzed. Attention is drawn to approaches to the preparation of spiro-fused compounds using reactions of intra-and intermolecular dearomatization of indoles. Recent advances in the synthesis of spiro-linked benzo heterocycles from derivatives of 2-olefin substituted anilines are summarized. The examples of the synthesis of spiro-fused heterocycles by means of metal complexes catalyzed decomposition of diazo compounds are given. Some syntheses of biologically active representatives are shown, as well as the use of transformations of spiroheterocycles in the preparation of other heterocycles.

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Section: Synthesis Of Spiroheterocycles From Arylamides Of Carboxylicsupporting

confidence: 52%

Section: Synthesis Of Spiroheterocycles From Arylamides Of Carboxylicmentioning

confidence: 99%

Advances in the Synthesis of Benzo‐Fused Spiro Nitrogen Heterocycles: New Approaches and Modification of Old Strategies

Гатауллин

2020

Helvetica Chimica Acta

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“…Most recently, Du group demonstrated a convenient route for the synthesis of C 3 ‐unsymmetric spirooxindoles 110 starting from the diphenylmalonamides 109 via intramolecular cyclization in the presence of PIDA ( 1 ). The cascade reaction proceeded by intramolecular oxidative C‐C bond followed by C‐N bond formation (Scheme ) …”

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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“…In 2018, Du and co‐workers developed a PIDA‐mediated cascade oxidative C−C/C−N bond formation reaction for the synthesis of C 3 ‐unsymmetrical spirooxindoles 170 (Figure ) . The reaction started with the nucleophilic attack from the oxygen center of the N ‐methylamide moiety to the iodine center of PIDA to give intermediate 171 .…”

Section: Cascade C−c/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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Cascade Formation of C₃‐Unsymmetric Spirooxindoles via PhI(OAc)₂‐Mediated Oxidative C−C/C−N Bond Formation

Cited by 13 publications

References 84 publications

Advances in the Synthesis of Benzo‐Fused Spiro Nitrogen Heterocycles: New Approaches and Modification of Old Strategies

Advances in the Synthesis of Benzo‐Fused Spiro Nitrogen Heterocycles: New Approaches and Modification of Old Strategies

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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Cascade Formation of C3‐Unsymmetric Spirooxindoles via PhI(OAc)2‐Mediated Oxidative C−C/C−N Bond Formation

Cited by 13 publications

References 84 publications

Advances in the Synthesis of Benzo‐Fused Spiro Nitrogen Heterocycles: New Approaches and Modification of Old Strategies

Advances in the Synthesis of Benzo‐Fused Spiro Nitrogen Heterocycles: New Approaches and Modification of Old Strategies

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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Product

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About

Cascade Formation of C₃‐Unsymmetric Spirooxindoles via PhI(OAc)₂‐Mediated Oxidative C−C/C−N Bond Formation