Pd-catalyzed synthesis of 3-(diarylmethylene)-2-oxindoles and 3-(arylmethylene)-2-oxindoles

Balalaie, Saeed; Motaghedi, Hassan; Bararjanian, Morteza; Tahmassebi, Daryoush; Bijanzadeh, Hamid Reza

doi:10.1016/j.tet.2011.09.089

Cited by 20 publications

(3 citation statements)

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“…The downsides of this synthetic technique are a lack of product variety and low efficiency. [18] Motivated by this method, Peshkov et al used 2-bromophenethylamines instead of 2-iodoaniline to construct 3-benzazepines. [19] In another similar publication, Bararjanian et al synthesized (Z)-3-(aminoarylmethylene)-oxindoles by replacing aniline with 2-iodoaniline, yielding Ugi adduct 23 (Scheme 9).…”

Section: Chemistryselectmentioning

confidence: 99%

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Annulation of the Ugi Products Using Palladium Catalysts

2022

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For almost half a century of efforts to make them, the importance of Ugi products has substantially expanded because they are used as precursors for the synthesis of more complex structures, such as peptides, amino acids, pharmaceutical compounds, and heterocycles. Through the introduction of a double or triple bond along with a carbon‐halide bond in the starting materials, the Ugi adduct can be cyclized through Pd‐catalyzed intramolecular reactions to create sophisticated heterocycles. This article discusses the role of palladium in the catalytic cyclization of the Ugi adducts and covers the published research from 2000 to 2022. Moreover, the proposed mechanisms of Pd‐catalyzed annulation of Ugi adducts are also reviewed.

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Section: Chemistryselectmentioning

confidence: 99%

“…In the absence of phenyl iodide, ( Z )‐monoarylmethylidene‐2‐oxindoles are formed. The downsides of this synthetic technique are a lack of product variety and low efficiency [18] . Motivated by this method, Peshkov et al .…”

Section: Synthesis Of Five‐membered Heterocyclesmentioning

confidence: 99%

Annulation of the Ugi Products Using Palladium Catalysts

2022

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“…The reactions were run in acetonitrile at room . 37 Recently, Qian and Zhang demonstrated an elegant goldcatalyzed oxidation/C-H functionalization reaction of tertiary N-arylpropiolamides 59 into 3-acylindolinone derivatives 60 (Scheme 19). In most cases, the nature of the substituents had no inuence on the results of this reaction.…”

Section: Synthesis Of 3-methyleneindolinones From Ortho-unsubstituted N-phenylpropiolamidesmentioning

confidence: 99%

Domino carbometalation/coupling reactions of N-arylpropiolamides: a novel and promising synthetic strategy toward stereocontrolled preparation of highly substituted 3-methyleneindolinones

Vessally

Hosseinzadeh‐Khanmiri

Ghorbani-Kalhor

et al. 2017

RSC Adv.

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A Half‐Century of the Ugi Reaction: Classic Variant

Ullrich

Kazmaier

2023

Organic Reactions

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The classic Ugi reaction is a four‐component coupling process that involves a carboxylic acid, a carbonyl compound, an amine, and an isocyanide. All reaction components are in a dynamic equilibrium with several intermediates, until an irreversible intramolecular 1,4‐ O → N acyl transfer leads to the formation of an N ‐acylamino acid amide. If chiral components are used in this reaction, a mixture of diastereomers is generally formed with moderate‐to‐low stereoselectivity. The broad scope of substrates that can be used in the Ugi reaction allows for the straightforward synthesis of libraries of structurally related amino acid and peptide derivatives. Therefore, this methodology is often applied to the synthesis of drugs, drug‐like molecules, and natural products. This chapter describes different variations of classic Ugi reactions, including the use of functionalized and cleavable reaction components to illustrate the broad scope of the reaction. In addition, applications in target‐directed synthesis and comparisons to other related multicomponent reactions are presented. Tabular surveys are organized according to the isocyanides used. The literature is discussed from the first disclosure of an Ugi reaction in 1961 through to the end of 2012.

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Pd-catalyzed synthesis of 3-(diarylmethylene)-2-oxindoles and 3-(arylmethylene)-2-oxindoles

Cited by 20 publications

References 57 publications

Annulation of the Ugi Products Using Palladium Catalysts

Annulation of the Ugi Products Using Palladium Catalysts

Domino carbometalation/coupling reactions of N-arylpropiolamides: a novel and promising synthetic strategy toward stereocontrolled preparation of highly substituted 3-methyleneindolinones

A Half‐Century of the Ugi Reaction: Classic Variant

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