Synthesis of heterocyclic compounds based on isatin through 1,3-dipolar cycloaddition reactions

Lashgari, Negar; Ziarani, Ghodsi Mohammadi

doi:10.3998/ark.5550190.0013.108

Cited by 136 publications

(42 citation statements)

References 13 publications

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“…The domino 1,3-dipolar cycloaddition reactions of azomethine ylides, generated in situ through the decarboxylative condensation of isatins and α-amino acids, with various dipolarophiles, are shown to be the most useful methodology for the regio-and stereoselective formation of a variety of complex 3,2 -spirooxindoles [69]. In 1970, Rizzi reported evidence for the formation of the nonstabilized azomethine ylide intermediate from the decarboxylative condensation between sarcosine and benzophenone.…”

Section: The Reaction Of 13-dipolar Cycloaddition With Azomethine Ylmentioning

confidence: 98%

Molecular diversity of spirooxindoles. Synthesis and biological activity

et al. 2015

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Spirooxindoles are important synthetic targets possessing extended biological activity and drug discovery applications. This review focuses on the various strategies for the enantioselective synthesis of spirocyclic oxindoles relying on reports over the past decade and from earlier work. The spirooxindoles in this review are separated into three structural classes, and then further categorized into the method type from which the spirocycle is generated.

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Section: The Reaction Of 13-dipolar Cycloaddition With Azomethine Ylmentioning

confidence: 98%

Molecular diversity of spirooxindoles. Synthesis and biological activity

et al. 2015

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“…[1][2][3] In recent years the azomethine ylide has gained a vital place in the synthesis of heterocyclic compounds as it serves as an important building block for the construction of nitrogen-containing five membered heterocycles, [4][5][6][7][8] which are often an integral part of many natural products and bioactive molecules. 9,10 The 3,3′-spirocyclooxindole skeleton is found in a growing number of natural or synthetic products presenting various biological activities.…”

Section: Introductionmentioning

confidence: 99%

Ultrasound-assisted, ZnBr2-catalyzed regio- and stereoselective synthesis of novel 3,3′-dispiropyrrolidine bisoxindole derivatives via 1,3-dipolar cycloaddition reaction of an azomethine ylide

Kiamehr¹,

Khodabakhshi²,

Moghaddam³

et al. 2017

Arkivoc

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Ultrasound irradiation in presence of 20% ZnBr2 effectively promotes regio-and stereo-selective cycloaddition reaction of azomethine ylide with a series of (E)-3-benzylideneindolin-2-ones to afford 3,3′-dispiropyrrolidine bisoxindole derivatives in excellent yields in methanol at room temperature. The factors affecting the cycloaddition reaction, for example solvent, catalyst, ultrasonic irradiation, are examined in detail to find the mildest conditions and highest reaction yields. The structure and stereochemistry of cycloadducts were determined by spectroscopic data and confirmed by X-ray crystallographic analysis.

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“…17 Synthesis of spiro 18 and multispiro 19 heterocyclic compounds from isatin were studied by Borad et al The enantioselective reactions of isatin were also the subject of several review articles. [20][21][22] Herein, in continuation of our studies towards isatin, [23][24][25] and since there is a wide range of reactions that include isatin in the synthesis of organic compounds, this review presents the recent applications of isatin in the synthesis of different types of organic compounds up to June 2016.…”

Section: Introductionmentioning

confidence: 99%