☆ 4.6 Review

1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides with Carbonyl Dipolarophiles Yielding Oxazolidine Derivatives

MOLECULES (2016)

期刊

MOLECULES

卷 21, 期 8, 页码 -

出版社

MDPI

DOI: 10.3390/molecules21080935

关键词

dipolar; cycloaddition; azomethine; ylide; carbonyl; aldehyde; ketone; anhydride; oxazolidine; spiro

类别

Biochemistry & Molecular Biology Chemistry, Multidisciplinary

资金

CSIRO Manufacturing

向作者/读者索取更多资源

Protocol

Reagent

摘要

We provide a comprehensive account of the 1,3-dipolar cycloaddition reactions of azomethine ylides with carbonyl dipolarophiles. Many different azomethine ylides have been studied, including stabilized and non-stabilized ylides. Of the carbonyl dipolarophiles, aldehydes including formaldehyde are the most studied, although there are now examples of cycloadditions with ketones, ketenes and carboxyl systems, in particular isatoic anhydrides and phthalic anhydrides. Intramolecular cycloadditions with esters can also occur under certain circumstances. The oxazolidine cycloadducts undergo a range of reactions triggered by the ring-opening of the oxazolidine ring system.

作者

我是这篇论文的作者

点击您的名字以认领此论文并将其添加到您的个人资料中。

评论

主要评分

4.6

评分不足

次要评分

新颖性

-

重要性

-

科学严谨性

-

评价这篇论文

推荐

Article Chemistry, Organic

Synthesis of Spiro{pyrrolidine-3,1′-pyrrolo[3,4-c]pyrrole} Basic Framework by Multicomponent 1,3-Dipolar Cycloaddition

Asmaa Belabbes, Veronica Selva, Francisco Foubelo, M. De Gracia Retamosa, Jose M. Sansano

Summary: The synthesis of complex spiro{pyrrolidine-3,1'-pyrrolo[3,4-c]pyrrole} skeleton under mild conditions is presented, with the order of addition of a primary amine and two equivalents of corresponding maleimide being crucial for high yields. The mechanism was studied by simple tests, revealing the Michael type addition of the amine onto the maleimide as a key step. Interesting scaffold hybrids were prepared through sequential addition of two different maleimides, and a more intriguing architecture was obtained through a metathesis reaction between allylic residues in the molecule precursor.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2021)

添加到收藏夹

Article Chemistry, Organic

[3+2] Dipolar Cycloaddition of a Stabilized Azomethine Ylide and an Electron-Deficient Dipolarophile: Revision of Regioselectivity

Kelvin J. Y. Wu, Amy E. Benedetto, Andrew G. Myers

Summary: The regioselectivity of a [3+2] dipolar cycloaddition reaction between a stabilized azomethine ylide and an electron-deficient dipolarophile is contrary to a previous report in this journal.

JOURNAL OF ORGANIC CHEMISTRY (2023)

添加到收藏夹

Article Chemistry, Multidisciplinary

1,3-Dipolar cycloaddition of polycyclic azomethine ylide to norcorroles: towards dibenzoullazine-fused derivatives

Sha Li, Yahan Sun, Xiaofang Li, Oskar Smaga, Sebastian Koniarz, Marcin Stepien, Piotr J. Chmielewski

Summary: A 1,3-cycloaddition reaction between 2-(tert-butyl)-8H-isoquinolino[4,3,2-de]phenanthridin-9-ium chloride and Ni-II norcorrole in the presence of base has been demonstrated to yield a family of chiral derivatives fused with pyrrole subunits of the macrocycle. Dehydrogenation of the cycloaddition products leads to dibenzoullazine ortho-fused antiaromatic porphyrinoids.

CHEMICAL COMMUNICATIONS (2022)

添加到收藏夹

Article Biochemistry & Molecular Biology

Diastereoselective Synthesis of Novel Spiro-Phosphacoumarins and Evaluation of Their Anti-Cancer Activity

Valeriia V. Sennikova, Alena Zalaltdinova, Yulia M. Sadykova, Ayrat R. Khamatgalimov, Almir S. Gazizov, Alexandra D. Voloshina, Anna P. Lyubina, Syumbelya K. Amerhanova, Julia K. Voronina, Elena A. Chugunova, Nurbol O. Appazov, Alexander R. Burilov, Michail A. Pudovik

Summary: We present a regio- and diastereoselective synthesis of novel pyrrolidine-fused spiro-dihydrophosphacoumarins through intermolecular [3 + 2] cycloaddition reaction. This method complements existing approaches and provides an easy way to obtain otherwise inaccessible derivatives. Additionally, we describe the unprecedented pathway of the reaction between 4-hydroxycoumarin and azomethine ylides. The most potent compound showed 2.6-fold higher anti-cancer activity against the HuTu 80 cell line compared to 5-fluorouracil, with a selectivity index > 32.

INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

1,3-Dipolar Cycloaddition of 3-Chromonyl-Substituted Glycine Imino Esters with Arylidenes and in situ Diastereodivergent via Retrocycloaddition

Mohammed F. F. Radwan, Elghareeb E. E. Elboray, Hemat M. M. Dardeer, Yusuke Kobayashi, Takumi Furuta, Shohei Hamada, Toshifumi Dohi, Moustafa F. F. Aly

Summary: 1,3-Dipolar cycloaddition through in situ generation of azomethine ylide provides a straightforward and critically important sustainable approach for access to diverse pyrrolidine chemical space. Metal-free AcOH-activated 1,3-dipolar cycloaddition protocol was developed to synthesize uncommon pyrrolidine cycloadducts with excellent diastereoselectivity. The reaction mechanism and the key role of AcOH were supported by experimental, theoretical and spectroscopic studies.

CHEMISTRY-AN ASIAN JOURNAL (2023)

添加到收藏夹

Article Biochemistry & Molecular Biology

Chemo-/Regio-Selective Synthesis of Novel Functionalized Spiro[pyrrolidine-2,3′-oxindoles] under Microwave Irradiation and Their Anticancer Activity

Richa Sharma, Lalit Yadav, Ali Adnan Nasim, Ravi Kant Yadav, Rui Hong Chen, Neha Kumari, Fan Ruiqi, Ashoke Sharon, Nawal Kishore Sahu, Sirish Kumar Ippagunta, Paolo Coghi, Vincent Kam Wai Wong, Sandeep Chaudhary

Summary: A series of spirooxindoles based on nitrostyrene were synthesized and shown to have promising in vitro anticancer activity against human lung and liver cancer cell lines.

MOLECULES (2023)

添加到收藏夹

Review Chemistry, Multidisciplinary

Catalytic Enantioselective [3+2] Cycloaddition of N-Metalated Azomethine Ylides

Sundaravel Vivek Kumar, Patrick J. Guiry

Summary: Asymmetric [3+2] cycloaddition reactions are interesting methods for synthesizing enantioenriched pyrrolidines with up to four stereocentres. Pyrrolidines are important compounds in biology and organocatalytic applications. This review summarizes the recent advancements in the enantioselective synthesis of pyrrolidines using metal catalysis, focusing on the [3+2] cycloadditions of azomethine ylides. The reactions are organized based on the type of metal catalysis and the complexity of the dipolarophile, highlighting their advantages and limitations.

CHEMISTRY-A EUROPEAN JOURNAL (2023)

添加到收藏夹

Article Chemistry, Applied

Copper-Catalyzed Chemo- and Diastereoselective 1,3-Dipolar Cycloaddition of Carbonyl Ylide and Aldehyde-Tethered-Cyclohexadienone to Access Polycyclic Systems

Shiyong Peng, Hong Zhang, Yuqi Zhu, Ting Zhou, Jieyin He, Nuan Chen, Ming Lang, Hongguang Li, Jian Wang

Summary: A copper-catalyzed tandem reaction was reported for the synthesis of oxapolycyclic frameworks via intermolecular ylide formation and intramolecular cycloaddition, providing moderate to excellent yields under mild conditions. The reaction creates two C-C bonds and one C-O bond, with five stereocentres including two all-carbon quaternary centres. Late-stage diversification of products can be achieved through chemoselective substitutions.

ADVANCED SYNTHESIS & CATALYSIS (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

exo′-Selective Construction of Spirobipyrrolidines by the Silver-catalyzed Asymmetric [3+2] Cycloaddition of Imino Esters with 4-Benzylidene-2,3-dioxopyrrolidines

Shohei Furuya, Kazuya Kanemoto, Shin-ichi Fukuzawa

Summary: This study describes an unprecedented Ag-catalyzed exo'-selective [3+2] cycloaddition reaction between imino esters and 4-benzylidene-2,3-dioxopyrrolidines. The reaction, efficiently catalyzed by Ag/(R, S-p)-ThioClickFerrophos (TCF), allows for the construction of spirobipyrrolidine scaffolds with excellent enantio- and diastereoselectivities. It is the first example of a silver-catalyzed exo'-selective asymmetric [3+2] cycloaddition and the first exo'-selective spirobipyrrolidine construction process using imino esters. The broad substrate scope of this reaction enables the synthesis of diverse spirobipyrrolidine derivatives, which are of interest for drug discovery. Mechanistic studies suggest that the unusual exo'-selectivity of this reaction is due to a stepwise Michael addition/Mannich sequence with bond rotation, rather than epimerization following the common exo- or endo-selective cycloaddition.

CHEMISTRY-AN ASIAN JOURNAL (2022)

添加到收藏夹

Article Chemistry, Physical

Regio- and stereoselective synthesis of dispiropyrrolizidines through 1,3-dipolar cycloaddition reaction: Inhibition of KRAS expression

Hooi Xian Lee, Wai Ming Li, Chee Wei Ang, Kerry Reimer, Victor Liu, Brian O. Patrick, Keng Yoon Yeong, Chow H. Lee

Summary: A facile three components (3 + 2) cycloaddition of two novel dispiropyrrolizidines was achieved, leading to unprecedented regioselectivity. The structures and activities of the synthesized compounds were determined through experimental techniques and structural analysis methods. The compounds exhibited the ability to down-regulate KRAS expression in human colorectal cancer cells.

JOURNAL OF MOLECULAR STRUCTURE (2022)

添加到收藏夹

Article Chemistry, Organic

Diastereodivergent 1,3-Dipolar Cycloaddition of α-Fluoro-α,β-Unsaturated Arylketones and Azomethine Ylides: Experimental and Theoretical DFT Studies

Subarna Jyoti Kalita, Zhen-Ni Zhao, Zi-Han Li, Feng Cheng, Yan Zhao, Yi-Yong Huang

Summary: Experimental and theoretical studies have investigated the 1,3-dipolar cycloaddition of alpha-fluoro-alpha, beta-unsaturated arylketones and azomethine ylides. The reaction proceeds in a diastereodivergent fashion, with the endo-selective pathway achieved using an Ag(I) catalyst. Theoretical DFT calculations suggest that the coordination between the silver atom and the carbonyl oxygen atom of the enone drives the endo-selectivity.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Facile preparation and preliminary cytotoxicity evaluation of dehydroepiandrosterone C-16 spiro-pyrrolidine derivatives

Hong-Wen Tao, Wen-Yu Peng, Jiang-Chun Yuan, Qiang Li, Lu-Yao Zeng, Xian-Yong Yu, Ping-Gui Yi

Summary: A facile synthesis of dehydroepiandrosterones derived by C-16 spiro-pyrrolidine and their cytotoxic evaluation were reported in this study. Seven derivatives were prepared by cycloaddition reaction and their cytotoxicity was evaluated by brine shrimp assay. Among them, two derivatives showed the best activities with LC50 values less than 10 μg/mL.

CHEMICAL PAPERS (2021)

添加到收藏夹

Article Chemistry, Organic

Green Stereoselective Synthesis and In Silico Anticancer Evaluation of Tetrahydro-β-carboline-Derived Spiro Heterocycles

Maneesh Mohan, Susan P. P. Eldhose, Athul Sudheendranath, E. G. Jayasree, Ani Deepthi

Summary: A green stereoselective synthesis of spiroheterocycles incorporating a spirooxindole and a 1,2,3,4-tetrahydro-beta-carboline (TH beta C) is demonstrated. The reaction is simple, chromatography-free, and yields densely substituted spiroheterocycles with excellent yields. In silico studies show that the compounds exhibit excellent binding interactions with MDM2 and PLK1 target proteins compared to reference drugs.

SYNTHESIS-STUTTGART (2023)

添加到收藏夹

Article Chemistry, Physical

Regio- and stereoselective synthesis of spiro-heterocycles bearing the pyrazole scaffold via [3+2] cycloaddition reaction

Mohammad Shahidul Islam, Matti Haukka, Saied M. Soliman, Abdullah Mohammed Al-Majid, A. F. M. Motiur Rahman, Ahmed Bari, Assem Barakat

Summary: A novel synthesis method for spirooxindoles engrafted with pyrazole skeleton was reported, using a one-pot multicomponent [3 + 2] cycloaddition reaction transformation. The regio- and diastereo-selectivity of the spiroheterocycles were elucidated through X-ray diffraction analysis, revealing the impact of short distance contacts on molecular packing and crystal stability. DFT calculations and NMR spectra analysis indicated the polar nature and electronic properties of the compounds, with good correlations between calculated and experimental data.

JOURNAL OF MOLECULAR STRUCTURE (2022)

添加到收藏夹

Review Biochemistry & Molecular Biology

1,3-Dipolar cycloaddition reactions of isatin-derived azomethine ylides for the synthesis of spirooxindole and indole-derived scaffolds: recent developments

Fatemeh Rostami Miankooshki, Mohammad Bayat, Shima Nasri, Narges Habibi Samet

Summary: This paper highlights the recent developments in the synthesis of spirooxindoles, focusing on representative synthetic methods and relevant reaction mechanisms from 2018 to 2021. It categorizes the synthetic methodologies based on the formation of azomethine ylide species from different starting materials.

MOLECULAR DIVERSITY (2023)

添加到收藏夹

Article Chemistry, Organic

1,3-Dipolar cycloaddition reactions of phthalic anhydrides with an azomethine ylide

Hugo Santos, Amy Distiller, Asha M. D'Souza, Quentin Arnoux, Jonathan M. White, Adam G. Meyer, John H. Ryan

ORGANIC CHEMISTRY FRONTIERS (2015)

添加到收藏夹

Article Agriculture, Multidisciplinary

Molecular Markers for Pyrethrin Autoxidation in Stored Pyrethrum Crop: Analysis and Structure Determination

Jamie A. Freemont, Stuart W. Littler, Oliver E. Hutt, Stephanie Mauger, Adam G. Meyer, David A. Winkler, Maurice G. Kerr, John H. Ryan, Helen F. Cole, Peter J. Duggan

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY (2016)

添加到收藏夹

Article Chemistry, Organic

Exploiting the Biginelli reaction: nitrogen-rich pyrimidine-based tercyclic α-helix mimetics

Zelong Lim, Peter J. Duggan, Soo San Wan, Guillaume Lessene, Adam G. Meyer, Kellie L. Tuck

TETRAHEDRON (2016)

添加到收藏夹

Article Chemistry, Organic

Kinetic Benchmarking Reveals the Competence of Prenyl Groups in Ring-Closing Metathesis

Karim A. Bahou, D. Christopher Braddock, Adam G. Meyer, G. Paul Savage

ORGANIC LETTERS (2017)

添加到收藏夹

Article Chemistry, Multidisciplinary

Competitive 1,3-Dipolar Cycloaddition Reactions of an Azomethine Ylide with Aromatic and Carbonyl Groups of Nitro-Substituted Isatoic Anhydrides

Asha M. D'Souza, Daniel J. Rivinoja, Roger J. Mulder, Jonathan M. White, Adam C. Meyer, Christopher J. T. Hyland, John H. Ryan

AUSTRALIAN JOURNAL OF CHEMISTRY (2018)

添加到收藏夹

Article Chemistry, Medicinal

Naturally occurring polyphenolic inhibitors of amyloid beta aggregation

Quentin I. Churches, Joanne Caine, Kate Cavanagh, Vidana Chandana Epa, Lynne Waddington, C. Elisabet Tranberg, Adam G. Meyer, Jose N. Varghese, Victor Streltsov, Peter J. Duggan

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2014)

添加到收藏夹

Article Chemistry, Organic

An iterative in silico and modular synthetic approach to aqueous soluble tercyclic α-helix mimetics

Zelong Lim, Peter J. Duggan, Adam G. Meyer, Kellie L. Tuck

ORGANIC & BIOMOLECULAR CHEMISTRY (2014)

添加到收藏夹

Article Chemistry, Organic

Benzoazepine-Fused Isoindolines via Intramolecular (3+2)-Cycloadditions of Azomethine Ylides with Dinitroarenes

Steven M. Wales, Daniel J. Rivinoja, Michael G. Gardiner, Melissa J. Bird, Adam G. Meyer, John H. Ryan, Christopher J. T. Hyland

ORGANIC LETTERS (2019)

添加到收藏夹

Article Chemistry, Organic

A Relay Strategy Actuates Pre-Existing Trisubstituted Olefins in Monoterpenoids for Cross-Metathesis with Trisubstituted Alkenes

Karim A. Bahou, D. Christopher Braddock, Adam G. Meyer, G. Paul Savage, Zhensheng Shi, Tianyou He

JOURNAL OF ORGANIC CHEMISTRY (2020)

添加到收藏夹

Article Chemistry, Organic

Relay Cross Metathesis for the Iterative Construction of Terpenoids and Synthesis of a Diterpene-Benzoate Macrolide of Biogenetic Relevance to the Bromophycolides

Karim A. Bahou, D. Christopher Braddock, Adam G. Meyer, G. Paul Savage

ORGANIC LETTERS (2020)

添加到收藏夹

Article Parasitology

An image-based Pathogen Box screen identifies new compounds with anti-Giardia activity and highlights the importance of assay choice in phenotypic drug discovery

Snigdha Tiash, Jake Saunders, Christopher J. S. Hart, John H. Ryan, Andrew G. Riches, Tina S. Skinner-Adams

INTERNATIONAL JOURNAL FOR PARASITOLOGY-DRUGS AND DRUG RESISTANCE (2020)

添加到收藏夹

Article Biochemistry & Molecular Biology

A Subset Screen of the Compounds Australia Scaffold Library Identifies 7-Acylaminodibenzoxazepinones as Potent and Selective Hits for Anti-Giardia Drug Discovery

Christopher J. S. Hart, Andrew G. G. Riches, Snigdha Tiash, Erin Clapper, Soumya Ramu, Johannes Zuegg, John H. H. Ryan, Tina S. S. Skinner-Adams

Summary: Giardia duodenalis infections are widespread and increasingly resistant to current treatments. This study screened the Compounds Australia Scaffolds Library and identified a series of compounds with potent and selective activity against Giardia parasites, including the promising compound SN00797640 which showed good in vivo tolerability and synergistic effects.

BIOMEDICINES (2022)

添加到收藏夹

Article Pharmacology & Pharmacy

Potent In Vitro Peptide Antagonists of the Thrombopoietin Receptor as Potential Myelofibrosis Drugs

Monika Szabo, Wioleta Kowalczyk, Anna Tarasova, Jessica Andrade, Cheang Ly Be, Roger Mulder, Jacinta White, Adam G. Meyer, Kjiana E. Schwab, Kellie Cartledge, Tu C. Le, Anoja Wickrama Arachchilage, Xiaoli Wang, Ronald Hoffman, Susan K. Nilsson, David N. Haylock, David A. Winkler

Summary: Myelofibrosis is a life-threatening blood cancer, and current drugs only provide symptomatic relief without altering the course of the disease. Inhibition of thrombopoietin, an important cytokine for platelet production, shows promise in slowing or stopping MF progression. Computational modeling and rational residue substitutions have identified a lead cyclic peptide, 48, as essential for activity at the c-Mpl receptor. These peptides are significant tools for in vivo analysis and a step towards disease-modifying therapies for MF.

ADVANCED THERAPEUTICS (2021)

添加到收藏夹

暂无数据

© Peeref 2019-2024. All rights reserved.