Different Behavior of 2-Substituted 3-Nitro-2<i>H</i>-chromenes in the Reaction with Stabilized Azomethine Ylides Generated from α-Iminoesters

Different Behavior of 2-Substituted 3-Nitro-2<i>H</i>-chromenes in the Reaction with Stabilized Azomethine Ylides Generated from α-Iminoesters

The AgOAc-catalysed reaction of 3-nitro-2-phenyl-2<i>H</i>-chromenes with stabilized azomethine ylides generated from the imines based on methyl glycinate and arylaldehydes leads to a mixture of <i>endo</i> and <i>endo</i>’ isomers of the corresponding chromeno[3,...

Full description

Bibliographic Details
Main Authors:	Ivan A. Kochnev, Alexey Y. Barkov, Nikita S. Simonov, Maria V. Ulitko, Nikolay S. Zimnitskiy, Vladislav Y. Korotaev, Vyacheslav Y. Sosnovskikh
Format:	Article
Language:	English
Published:	MDPI AG 2022-12-01
Series:	Molecules
Subjects:	3-nitro-2<i>H</i>-chromenes azomethine ylides Michael addition/Mannich reaction sequence chromeno[3,4-<i>c</i>]pyrrolidines cytotoxicity
Online Access:	https://www.mdpi.com/1420-3049/27/24/8983

Similar Items

Azomethine Ylides—Versatile Synthons for Pyrrolidinyl-Heterocyclic Compounds
by: Siva S. Panda, et al.
Published: (2023-01-01)

Green and Efficient Construction of Chromeno[3,4-<i>c</i>]pyrrole Core via Barton–Zard Reaction from 3-Nitro-2<i>H</i>-chromenes and Ethyl Isocyanoacetate
by: Ivan A. Kochnev, et al.
Published: (2022-12-01)

Diversity-Oriented Synthesis of Novel Trihalomethyl-Containing Spirochromeno[3,4-a](thia)pyrrolizidines and Spirochromeno-[3,4-a]indolizidines by One-Pot, Three-Component [3+2]-Cycloaddition Reaction
by: Igor B. Kutyashev, et al.
Published: (2021-01-01)

Highly Efficient Construction of Sugar-Fused Spirochromanono Pyrrolidines/Pyrrolizidines/Thiolizidines via 1,3-Dipolar Cycloaddition of Azomethine Ylides
by: Sirisha Nallamala, et al.
Published: (2017-03-01)

Stereoselective cyclo-addition reactions of azomethine ylides catalysed by in situ generated Ag(I)/bisphosphine complexes
by: VLADIMIR SAVIĆ, et al.
Published: (2010-01-01)

Additive-assisted regioselective 1,3-dipolar cycloaddition of azomethine ylides with benzylideneacetone
by: Chuqin Peng, et al.
Published: (2014-02-01)

Nitropyridines as 2π-Partners in 1,3-Dipolar Cycloadditions with N-Methyl Azomethine Ylide: An Easy Access to Condensed Pyrrolines
by: Maxim A. Bastrakov, et al.
Published: (2021-09-01)

Chromene- and Quinoline-3-Carbaldehydes: Useful Intermediates in the Synthesis of Heterocyclic Scaffolds
by: Djenisa H. A. Rocha, et al.
Published: (2020-08-01)

One-Pot Synthesis of Triazolobenzodiazepines Through Decarboxylative [3 + 2] Cycloaddition of Nonstabilized Azomethine Ylides and Cu-Free Click Reactions
by: Xiaoming Ma, et al.
Published: (2019-02-01)

1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides with Carbonyl Dipolarophiles Yielding Oxazolidine Derivatives
by: Adam G. Meyer, et al.
Published: (2016-07-01)

Synthesis of bis-spirocyclic derivatives of 3-azabicyclo[3.1.0]hexane via cyclopropene cycloadditions to the stable azomethine ylide derived from Ruhemann's purple
by: Alexander S. Filatov, et al.
Published: (2022-06-01)

Copper-Catalyzed Asymmetric Dearomative [3+2] Cycloaddition of Nitroheteroarenes with Azomethines
by: Yan Chen, et al.
Published: (2023-03-01)

[3+2]-Cycloaddition of azomethine ylides to 5-methylidene-3-aryl-2-сhalcogen-imidazolones: access to dispiro indolinone-pyrrolidine-imidazolones
by: Maxim E. Kukushkin, et al.
Published: (2022-03-01)

11<i>H</i>-Benzo[4,5]imidazo[1,2-<i>a</i>]indol-11-one as a New Precursor of Azomethine Ylides: 1,3-Dipolar Cycloaddition Reactions with Cyclopropenes and Maleimides
by: Alexander S. Filatov, et al.
Published: (2022-10-01)

A Molecular Electron Density Theory Study of the [3+2] Cycloaddition Reaction of <i>Pseudo(mono)radical</i> Azomethine Ylides with Phenyl Vinyl Sulphone
by: Mar Ríos-Gutiérrez, et al.
Published: (2022-06-01)

A Molecular Electron Density Theory Study of the [3+2] Cycloaddition Reaction of an Azomethine Ylide with an Electrophilic Ethylene Linked to Triazole and Ferrocene Units
by: Luis R. Domingo, et al.
Published: (2022-10-01)

A Diastereoselective Synthesis of Dispiro[oxindole-cyclohexanone]pyrrolidines by 1,3-Dipolar Cycloaddition
by: Alexander Anis’kov, et al.
Published: (2017-12-01)

Piperazine-Amberlyst®15-catalysed synthesis of 2-amino-4H-chromenes, chromeno[2,3-b]pyridines and chromeno[2,3-d]pyrimidines
by: Giovanna Bosica, et al.
Published: (2023-01-01)

A Facile One-Pot Construction of Succinimide-Fused Spiro[Pyrrolidine-2,3′-Oxindoles] via 1,3-Dipolar Cycloaddition Involving 3-Amino Oxindoles and Maleimides
by: Lunqiang Jin, et al.
Published: (2018-03-01)

[3+2] Cycloaddition Reaction for the Stereoselective Synthesis of a New Spirooxindole Compound Grafted Imidazo[2,1-<em>b</em>]thiazole Scaffold: Crystal Structure and Computational Study
by: Mezna Saleh Altowyan, et al.
Published: (2021-12-01)

Chemo-/Regio-Selective Synthesis of Novel Functionalized Spiro[pyrrolidine-2,3′-oxindoles] under Microwave Irradiation and Their Anticancer Activity
by: Richa Sharma, et al.
Published: (2023-09-01)

K<sub>2</sub>CO<sub>3</sub>-Promoted Formal [3+3]-Cycloaddition of <i>N</i>-Unsubstituted Isatin <i>N</i>,<i>N′</i>-Cyclic Azomethine Imine 1,3-Dipoles with Knoevenagel Adducts
by: Guosheng Yang, et al.
Published: (2023-01-01)

Diastereoselective Synthesis of Dispiro[Imidazothiazolotriazine-Pyrrolidin-Oxindoles] and Their Isomerization Pathways in Basic Medium
by: Alexei N. Izmest′ev, et al.
Published: (2023-11-01)

Three-Component Access to Functionalized Spiropyrrolidine Heterocyclic Scaffolds and Their Cholinesterase Inhibitory Activity
by: Sarra Boudriga, et al.
Published: (2020-04-01)

A Facile Synthesis of Functionalized Dispirooxindole Derivatives via a Three-Component 1,3-Dipolar Cycloaddition Reaction
by: Liang Ouyang, et al.
Published: (2013-05-01)

New Nitro-Laterally Substituted Azomethine Derivatives; Synthesis, Mesomorphic and Computational Characterizations
by: Mohamed A. El-atawy, et al.
Published: (2021-03-01)

Synthesis of Unexpected Dimethyl 2-(4-Chlorophenyl)-2,3-dihydropyrrolo[2,1-<em>a</em>]isoquinoline-1,3-dicarboxylate via Hydrolysis/Cycloaddition/Elimination Cascades: Single Crystal X-ray and Chemical Structure Insights
by: Mezna Saleh Altowyan, et al.
Published: (2021-12-01)

Oxidative Cyclization of 5<i>H</i>-Chromeno[2,3-<i>b</i>]pyridines to Benzo[<i>b</i>]chromeno[4,3,2-<i>de</i>][1,6]naphthyridines, Their NMR Study and Computer Evaluation as Material for LED
by: Yuliya E. Ryzhkova, et al.
Published: (2022-06-01)

Stereoselective Synthesis of the Di-Spirooxindole Analogs Based Oxindole and Cyclohexanone Moieties as Potential Anticancer Agents
by: Abdullah Mohammed Al-Majid, et al.
Published: (2021-10-01)

Synthesis, Structure and Stereochemistry of Dispirocompounds Based on Imidazothiazolotriazine and Pyrrolidineoxindole
by: Alexei N. Izmest’ev, et al.
Published: (2022-11-01)

Synthesis of New N-Phthalimide Substituted Tricyclic Imide Containing Isoxazoline and Bispiro Functional Group as Possible Anti-cancer Agents
by: Ömer Tahir Günkara, et al.
Published: (2017-11-01)

An Efficient Synthesis of Novel Dispirooxindole Derivatives via One-Pot Three-Component 1,3-Dipolar Cycloaddition Reactions
by: Yucheng Wang, et al.
Published: (2012-10-01)

Diverse Synthesis of Fused Polyheterocyclic Compounds via [3 + 2] Cycloaddition of In Situ-Generated Heteroaromatic <i>N</i>-Ylides and Electron-Deficient Olefins
by: Zhen-Hua Wang, et al.
Published: (2023-05-01)

Synthesis of 6,7-Dihydro-1<i>H</i>,5<i>H</i>-pyrazolo[1,2-<i>a</i>]pyrazoles by Azomethine Imine-Alkyne Cycloadditions Using Immobilized Cu(II)-Catalysts
by: Urša Štanfel, et al.
Published: (2021-01-01)

Efficient Synthesis of 3-Sulfonyl-2-sulfonylmethyl-2<i>H</i>-chromenes via Tandem Knoevenagel Condensation/Oxa-Michael Addition Protocol
by: Lin Jiang, et al.
Published: (2022-04-01)

Density Functional Theory Calculations: A Useful Tool to Investigate Mechanisms of 1,3-Dipolar Cycloaddition Reactions
by: Maria Assunta Chiacchio, et al.
Published: (2024-01-01)

Crystal structure of 3′-(1H-indole-3-carbonyl)-1′-methyl-2-oxo-4′-(4-oxo-4H-chromen-3-yl)spiro[indoline-3,2′-pyrrolidine]-3′-carbonitrile
by: M. P. Savithri, et al.
Published: (2015-11-01)

Enantioselective 1,3-Dipolar Cycloaddition Using (<i>Z</i>)-α-Amidonitroalkenes as a Key Step to the Access to Chiral <i>cis</i>-3,4-Diaminopyrrolidines
by: Eduardo García-Mingüens, et al.
Published: (2022-07-01)

Triethylamine-Promoted Oxidative Cyclodimerization of 2<i>H</i>-Azirine-2-carboxylates to Pyrimidine-4,6-dicarboxylates: Experimental and DFT Study
by: Timofei N. Zakharov, et al.
Published: (2023-05-01)

Synthesis of fused tricyclic amines unsubstituted at the ring-junction positions by a cascade condensation, cyclization, cycloaddition then decarbonylation strategy
by: Iain Coldham, et al.
Published: (2012-01-01)