Highly regio- and stereoselective 1,3-dipolar cycloaddition of stabilised azomethine ylides to 3,3,3-trihalogeno-1-nitropropenes: synthesis of trihalomethylated spiro[indoline-3,2′-pyrrolidin]-2-ones and spiro[indoline-3,3′-pyrrolizin]-2-ones

Barkov, Alexey Yu.; Zimnitskiy, Nikolay S.; Korotaev, Vladislav Yu.; Kutyashev, Igor B.; Moshkin, Vladimir S.; Sosnovskikh, Vyacheslav Ya.

doi:10.1016/j.tet.2016.09.017

Cited by 31 publications

(13 citation statements)

References 57 publications

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“…The derivatives of 2‐oxo‐3‐methylidene indole, [167–173] azaaurone, [174] can be effectively used in the synthesis of spirocyclic systems. Often, approaches are also used that lead, along with the creation of a spirocyclic fragment, to the violation of the π‐conjugation of the pyrrole ring of indole, as well as to the buildup of a heterocyclic unit on the backbone of 2‐indolone or its 2‐thio analog.…”

Section: Syntheses Of Spiroheterocycles From 3‐alkylidene‐indol‐2‐onementioning

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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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: Syntheses Of Spiroheterocycles From 3‐alkylidene‐indol‐2‐onementioning

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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“…36 Dispirooxindolepyrrolidines 71 were reported by Singh et al and prepared from sarcosine (13) and isatins 2 with 1aryl-3-benzylidenepyrrolidine-2,5-diones 70 as dipolarophiles; the products 71 were diastereoselectively isolated in high yields (Scheme 18). 37 Glycine (17) or sarcosine (13) with isatins 2, 38 or even proline 1 plus acenaphthoquinone (33) or indenoquinoxaline-11-one 43 were also utilized in the presence of dipolarophiles 70. 39 Spirooxindolepyrrolizidines 73 and 74, derived from isatins 2 or acenaphthoquinone (33), respectively, bearing a withaferin-A system were isolated by Mondal and co-workers.…”

Section: Short Review Syn Thesismentioning

confidence: 99%

“…11 Alkylidene-oxazolones 15 were selected as dipolarophiles to synthesize biologically important spirooxindole frameworks 16. Diverse isatins 2 and a variety of amino acids such as glycine (17), sarcosine (13), L-proline (1), or thiazolidine-4-carboxylic acid (18), afforded, in a one-pot, three-component process, a regio-and diastereoselective 1,3-DC (Scheme 5). Biological evaluation of compounds 16 against several cancer cell-lines revealed that some of them possessed anti-tumor activity.…”

Section: Introductionmentioning

confidence: 99%

Current Trends towards the Synthesis of Bioactive Heterocycles and Natural Products Using 1,3-Dipolar Cycloadditions (1,3-DC) with Azomethine Ylides

2017

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In this revision a summary of the trends of the formation of complex or not so complex heterocyclic structures through 1,3-DC of azomethine ylides is described. Diastereo-and enantioselective processes as well as nonasymmetric cycloadditions constitute very important synthetic tools for achieving all these series of compounds. The contents are classified as follows: 1. Introduction 2. Synthesis of spiroxindoles 3. Synthesis of spiropyrrolidines 4. Synthesis of spiropiperidines and piperidines 5. Synthesis of pyrrolidines and fused pyrrolidines 6. Synthesis of pyrrolizidines and indolizidines 7. Synthesis of quinolone and isoquinolines 8. Conclusions

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“…[ 10,11 ] Hence many reports are available in the literature for such cycloadditions, especially by using electron‐deficient alkenes and alkynes as dipolarophiles such as α,β‐unsaturated carbonyl compounds and nitro compounds. [ 12–15 ] The resulting adducts find enormous applications in pharmaceutics, catalysis, and agrochemicals. [ 16,17 ]…”

Section: Introductionmentioning

confidence: 99%

One‐pot three‐component 1,3‐dipolar cycloaddition of azomethineylides to nitrofuran containing acetylenic ketones and molecular docking studies of the cycloadducts

Kadambar

Kalluraya

Kumar

2020

Journal of Heterocyclic Chem

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One‐pot three‐component 1,3‐dipolar cycloaddition reaction of azomethineylides generated from various combinations of isatin and ninhydrin with α‐aminoacids to 5‐nitrofurancontaining acetylenic ketones was carried out under thermal and microwave methods. The study of the regiochemical trend during the cycloaddition suggested that the nitrofuran ring exert no effect on the regiochemistry of the reaction as observed in the case of nitrofuran containing chalcones. The reason for the nil influence of the nitrofuran group is attributed to the increased electron density due to the triple bond. The newly synthesized compounds were docked to the active site of human anaplastic lymphoma kinase (ALK) to know the cancer cell toxicity in silico. The compounds 4b and 5a showed good binding interactions with the target in the active site.

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Highly regio- and stereoselective 1,3-dipolar cycloaddition of stabilised azomethine ylides to 3,3,3-trihalogeno-1-nitropropenes: synthesis of trihalomethylated spiro[indoline-3,2′-pyrrolidin]-2-ones and spiro[indoline-3,3′-pyrrolizin]-2-ones

Cited by 31 publications

References 57 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

Current Trends towards the Synthesis of Bioactive Heterocycles and Natural Products Using 1,3-Dipolar Cycloadditions (1,3-DC) with Azomethine Ylides

One‐pot three‐component 1,3‐dipolar cycloaddition of azomethineylides to nitrofuran containing acetylenic ketones and molecular docking studies of the cycloadducts

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