Cargando…

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

A reliable method for the synthesis of bis-spirocyclic derivatives of 3-azabicyclo[3.1.0]hexanes through the 1,3-dipolar cycloaddition (1,3-DC) reactions of cyclopropenes to the stable azomethine ylide – protonated form of Ruhemann's purple (PRP) has been developed. Both 3-substituted and 3,3-d...

Descripción completa

Detalles Bibliográficos
Autores principales:	Filatov, Alexander S, Khoroshilova, Olesya V, Larina, Anna G, Boitsov, Vitali M, Stepakov, Alexander V
Formato:	Online Artículo Texto
Lenguaje:	English
Publicado:	Beilstein-Institut 2022
Materias:	Full Research Paper
Acceso en línea:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9263550/ https://www.ncbi.nlm.nih.gov/pubmed/35859623 http://dx.doi.org/10.3762/bjoc.18.77

Ejemplares similares

11H-Benzo[4,5]imidazo[1,2-a]indol-11-one as a New Precursor of Azomethine Ylides: 1,3-Dipolar Cycloaddition Reactions with Cyclopropenes and Maleimides
por: Filatov, Alexander S., et al.
Publicado: (2022)

Identification of Spiro-Fused [3-azabicyclo[3.1.0]hexane]oxindoles as Potential Antitumor Agents: Initial In Vitro Evaluation of Anti-Proliferative Effect and Actin Cytoskeleton Transformation in 3T3 and 3T3-SV40 Fibroblast
por: Knyazev, Nickolay A., et al.
Publicado: (2021)

Synthesis of bicyclo[3.1.0]hexanes by (3 + 2) annulation of cyclopropenes with aminocyclopropanes
por: Muriel, Bastian, et al.
Publicado: (2019)

Biological Evaluation of 3-Azaspiro[Bicyclo[3.1.0]Hexane-2,5′-Pyrimidines] as Potential Antitumor Agents
por: Shmakov, Stanislav V., et al.
Publicado: (2022)

Synthesis of CHF(2)-substituted 3-azabicyclo[3.1.0]hexanes by photochemical decomposition of CHF(2)-pyrazolines
por: Zheng, Yang, et al.
Publicado: (2018)

[3 + 2] cycloaddition of nonstabilized azomethine ylides and 2-benzothiazolamines to access imidazolidine derivatives
por: Wang, Kai-Kai, et al.
Publicado: (2022)

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

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

[3 + 2] Cycloaddition with photogenerated azomethine ylides in β-cyclodextrin
por: Sohora, Margareta, et al.
Publicado: (2020)

Strain‐Release Driven Spirocyclization of Azabicyclo[1.1.0]butyl Ketones
por: Tyler, Jasper L., et al.
Publicado: (2021)

Dearomative [3 + 2] cycloaddition reaction of nitrobenzothiophenes with nonstabilized azomethine ylides
por: Wang, Kai-Kai, et al.
Publicado: (2020)

Chemistry of polyhalogenated nitrobutadienes, 10: Synthesis of highly functionalized heterocycles with a rigid 6-amino-3-azabicyclo[3.1.0]hexane moiety
por: Zapol’skii, Viktor A, et al.
Publicado: (2012)

Cyclopropene derivatives of aminosugars for metabolic glycoengineering
por: Hassenrück, Jessica, et al.
Publicado: (2019)

Strain‐Release‐Driven Friedel–Crafts Spirocyclization of Azabicyclo[1.1.0]butanes
por: Tyler, Jasper L., et al.
Publicado: (2021)

Additive-assisted regioselective 1,3-dipolar cycloaddition of azomethine ylides with benzylideneacetone
por: Peng, Chuqin, et al.
Publicado: (2014)

Polycyclic aromatic azomethine ylides: a unique entry to extended polycyclic heteroaromatics
por: Berger, Reinhard, et al.
Publicado: (2015)

Synergistic catalysis for cascade allylation and 2-aza-cope rearrangement of azomethine ylides
por: Wei, Liang, et al.
Publicado: (2019)

Mechanistic studies and radiofluorination of structurally diverse pharmaceuticals with spirocyclic iodonium(iii) ylides
por: Rotstein, Benjamin H., et al.
Publicado: (2016)

Exploration of pyrazine-embedded antiaromatic polycyclic hydrocarbons generated by solution and on-surface azomethine ylide homocoupling
por: Wang, Xiao-Ye, et al.
Publicado: (2017)

Intramolecular [3 + 2]-Cycloadditions of Azomethine Ylides Derived from Secondary Amines via Redox-Neutral C–H Functionalization
por: Mantelingu, Kempegowda, et al.
Publicado: (2014)

Intramolecular Hydrogen Bond Activation: Thiourea-Organocatalyzed Enantioselective 1,3-Dipolar Cycloaddition of Salicylaldehyde-Derived Azomethine Ylides with Nitroalkenes
por: Esteban, Francisco, et al.
Publicado: (2018)

Catalytic Enantioselective 1,3-Dipolar Cycloadditions of Azomethine Ylides for Biology-Oriented Synthesis
por: Narayan, Rishikesh, et al.
Publicado: (2014)

Enantioselective, Decarboxylative (3+2)-Cycloaddition of Azomethine Ylides and Chromone-3-Carboxylic Acids
por: Kowalska, Ewelina, et al.
Publicado: (2022)

Catalytic Synthesis of Trifluoromethyl Cyclopropenes and Oligo‐Cyclopropenes
por: Tran, Uyen P. N., et al.
Publicado: (2020)

Ethyl 2-(4-methoxyphenyl)-6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate: crystal structure and Hirshfeld analysis
por: Zukerman-Schpector, Julio, et al.
Publicado: (2017)

In silico identification and molecular dynamic simulations of derivatives of 6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide against main protease 3CL(pro) of SARS-CoV-2 viral infection
por: Sinha, Prashasti, et al.
Publicado: (2023)

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

Catalyst-Free [3+2] Cycloaddition of Electron-Deficient Alkynes and o-Hydroxyaryl Azomethine Ylides in Water
por: Zhu, Jin, et al.
Publicado: (2020)

Diastereoselective synthesis of dispirooxindoles via [3+2] cycloaddition of azomethine ylides to 3-phenacylideneoxindoles and evaluation of their cytotoxicity
por: Huang, Ying, et al.
Publicado: (2018)

Copper(I)-catalyzed asymmetric 1,3-dipolar cycloaddition of 1,3-enynes and azomethine ylides
por: Wang, Bo-Ran, et al.
Publicado: (2023)

Metal-Dependent Umpolung Reactivity of Carbenes Derived from Cyclopropenes
por: Zhang, Dan, et al.
Publicado: (2019)

Spirocyclic derivatives as antioxidants: a review
por: Acosta-Quiroga, Karen, et al.
Publicado: (2021)

A New Entry to Azomethine Ylides from Allylic Amines and Glyoxals: Shifting the Reliance on Amino Ester Precursors
por: Machamer, Natalie K., et al.
Publicado: (2014)

Application of 1,3‐Dipolar Reactions between Azomethine Ylides and Alkenes to the Synthesis of Catalysts and Biologically Active Compounds
por: Arrastia, Iosune, et al.
Publicado: (2018)

Synthesis of bioactive fluoropyrrolidines via copper(i)-catalysed asymmetric 1,3-dipolar cycloaddition of azomethine ylides
por: Xu, Xiao, et al.
Publicado: (2021)

Synthesis of diversely substituted bis-pyrrolizidino/ thiopyrrolizidino oxindolo/acenaphthyleno curcuminoids via sequential azomethine ylide cycloaddition
por: Singh, Meenakshi, et al.
Publicado: (2018)

General Pyrrolidine Synthesis via Iridium-Catalyzed Reductive Azomethine Ylide Generation from Tertiary Amides and Lactams
por: Yamazaki, Ken, et al.
Publicado: (2021)

Exploration of Spirocyclic Derivatives of Ciprofloxacin as Antibacterial Agents
por: Lukin, Alexei, et al.
Publicado: (2022)

The Azomethine Ylide Route to Amine C–H Functionalization: Redox-Versions of Classic Reactions and a Pathway to New Transformations
por: Seidel, Daniel
Publicado: (2015)

Heterogeneous graphene oxide as recyclable catalyst for azomethine ylide mediated 1,3 dipolar cycloaddition reaction in aqueous medium
por: Reddy, Marri Sameer, et al.
Publicado: (2018)

Cannot write session to /tmp/vufind_sessions/sess_ke7cl1bjnr18ol8klpinnf6oeu