1,3-Dipolar Cycloaddition of 3-Amino Oxindole-Based Azomethine Ylides and O-Vinylphosphonylated Salicylaldehydes for Diastereoselective Synthesis of Oxindole Spiro-P,N-polycyclic Heterocycles

Synthesis ◽  
2020 ◽  
Vol 52 (09) ◽  
pp. 1387-1397
Author(s):  
Mingshu Wu ◽  
Dulin Kong ◽  
Tiao Huang ◽  
Li Liu ◽  
Qinghe Wang
Keyword(s):  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Diastereoselective Synthesis ◽  
Atom Economy ◽  
Assembly Strategy

An efficient stereoselective assembly strategy for the construction of pyrrolidin-2,3′-oxindole cis-fused phosphadihydrocoumarins was established. The process involves the condensation of O-vinylphosphonylated salicylaldehydes and 3-amino oxindoles followed by intermolecular cycloaddition with high diastereoselectivity and atom economy.

scholarly journals Diastereoselective synthesis of dispirooxindoles via [3+2] cycloaddition of azomethine ylides to 3-phenacylideneoxindoles and evaluation of their cytotoxicity

RSC Advances ◽  
2018 ◽  
Vol 8 (42) ◽  
pp. 23990-23995 ◽  
Author(s):  
Ying Huang ◽  
Yi-Xin Huang ◽  
Jing Sun ◽  
Chao-Guo Yan
Keyword(s):  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Diastereoselective Synthesis ◽  
Three Component Reaction

The three-component reaction of 1,2,3,4-tetrahydroisoquinoline, isatins and 3-phenacylideneoxindoles in refluxing ethanol afforded dispiro[indoline-3,1′-pyrrolo[2,1-a]isoquinoline-3′,3′-indolines] (4a–4x) in good yields via 1,3-dipolar cycloaddition.

A Novel Four-Component Reaction for the Diastereoselective Synthesis of Some New Spiro Pyrrolizidines via 1,3-Dipolar Cycloaddition of Azomethine Ylides

Synthesis ◽  
2004 ◽  
Vol 2004 (14) ◽  
pp. 2263-2265 ◽  
Author(s):  
Javad Azizian ◽  
Ali Reza Karimi ◽  
Ali A. Mohammadi ◽  
Mohammad R. Mohammadizadeh
Keyword(s):  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Diastereoselective Synthesis

scholarly journals Synthesis of polysubstituted spiropyrrolidines using 2-acetylfuran, 2-acetylthiophene, and 2-acetylpyrrole

2021 ◽  
Vol 21 (3) ◽  
pp. 254-259
Author(s):  
Svetlana V. Borisova ◽  
◽  
Vitaly V. Sorokin ◽  
Keyword(s):  
13C Nmr Spectroscopy ◽  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Knoevenagel Reaction ◽  
Atom Economy ◽  
Reaction Conditions ◽  
Stereo Selectivity ◽  
Decarboxylative Condensation ◽  
First Time

A series of novel spirooxindoles have been synthesized through three-component 1,3-dipolar cycloaddition of azomethine ylides generated in situ by the decarboxylative condensation of isatin and sarcosine with the dipolarophile 3-phenyl-1-(heteroaryl -2-yl)prop-2-en-1- one, synthesized by the Knoevenagel reaction using 2-acetylfuran, 2-acetylpyrrole, 2-acetylthiophene and substituted benzaldehydes. These compounds are used for the first time as dipolarophiles. This method has the advantages of mild reaction conditions, high atom economy, excellent yields, and high regio- and stereo-selectivity. The reaction was carried out by mixing equimolar amounts of enone and isatin, as well as a slight excess of sarcosine in isopropyl alcohol when heated to 60–70°C. Among the enones with various heterocyclic substituents, it is most convenient to use compounds containing a pyrrole fragment as dipolarophiles, since the products are obtained in a short amount of time in good yields. The use of enones obtained from 2-acetylthiophene leads to an increase in the reaction time, and from 2-acetylfuran - to a significant resinification of the reaction mixture. The structures of the compounds obtained were proved using a combination of 1H, 13C NMR spectroscopy data, as well as two-dimensional NMR experiments of heteronuclear correlation, HSQC and HMBC. Based on the data obtained, a mechanism for the formation of products has been proposed.

Azomethine Ylide Cycloaddition of 1,3- dienyl esters: Highly regio- and diastereoselective synthesis of functionalized pyrrolidinochromenes

2022 ◽  
Author(s):  
Manickam Bakthadoss ◽  
Mohammad Mushaf ◽  
Vishal Agarwal ◽  
Tadiparthi Thirupathi Reddy ◽  
Duddu Savaraiah Sharada
Keyword(s):  
Azomethine Ylides ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
Diastereoselective Synthesis

An efficient protocol for the synthesis of tricyclic pyrolidinochromenes has been developed via an intramolecular 1,3-dipolar cycloaddition of azomethine ylides generated in situ from 1,3- dienyl ester tethered O-hydroxyarylaldehyde and...

Diastereoselective synthesis of indolenine-based spiro[pyrazolone-4,2’-pyrrolidine] scaffolds via 1,3-dipolar cycloaddition of 4-aminopyrazolones, aldehydes, and indolenines

2021 ◽  
Author(s):  
Baomin Wang ◽  
Shah Nawaz ◽  
Shiqiang Wei ◽  
Yue Huang ◽  
Wenyao Wang ◽  
...  
Keyword(s):  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Diastereoselective Synthesis ◽  
One Pot

In this work, we report a novel one-pot [3+2] cycloaddition of 4-aminopyrazolones, indolenines, and aldehydes. The reaction utilized the in-situ generated azomethine ylides as 1,3-dipoles and 2-alkenylindolenines as dipolarophiles affording...

An Experimental and Theoretical Study of the 1,3-Dipolar Cycloaddition of Alloxan-Derived Azomethine Ylides to Cyclopropenes

Synthesis ◽  
2021 ◽  
Author(s):  
Alexander Vladimirovich Stepakov ◽  
Vitali Boitsov ◽  
Alexander Filatov ◽  
Stanislav Selivanov ◽  
Stanislav Shmakov ◽  
...  
Keyword(s):  
Density Functional ◽  
Theoretical Study ◽  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Diastereoselective Synthesis ◽  
K562 Cell Line ◽  
Functional Theory ◽  
Shed Light ◽  
Mts Assay

A diastereoselective synthesis of biologically interesting spirobarbiturates has been achieved via [3 + 2] cycloaddition of alloxan-derived azomethine ylides to 3-R-1,2-diphenylcyclopropenes. With this approach, various spirobarbiturate-3-azabicyclo[3.1.0]hexanes and spirobarbiturate-cyclopropa[a]pyrrolizines were obtained in moderate to good yields with excellent diastereoselectivities. DFT calculations (M11 density functional theory) have been carried out to shed light on the molecular mechanism of 1,3-dipolar cycloaddition of alloxan-derived azomethine ylides to cyclopropenes. The cytotoxic activity of some obtained compounds against human erythroleukemia (K562) cell line was evaluated in vitro by MTS-assay.

Diastereoselective Synthesis of Pyrazolines by Metal-Free Rearrangement of Bicyclic Triazolines

Synthesis ◽  
2020 ◽  
Vol 52 (19) ◽  
pp. 2892-2898
Author(s):  
Sara Pellegrino ◽  
Emanuela Erba ◽  
Raffaella Bucci ◽  
Francesca Clerici
Keyword(s):  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Diastereoselective Synthesis ◽  
Atom Economy ◽  
Metal Free ◽  
Synthetic Procedure

The metal-free preparation of diazoalkanes through the ring rearrangement of bicyclic triazolines is reported here. Their use in 1,3-dipolar cycloaddition reactions with electron-withdrawing alkenes was investigated. This synthetic procedure allows differently substituted pyrazolines to be obtained in few steps and with high atom economy.

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