Straightforward and Highly Diastereoselective Synthesis of a New Set of Functionalized Dispiropyrrolidines Involving Multicomponent 1,3‐Dipolar Cycloaddition with Azomethine Ylides

2019 ◽  
Vol 56 (6) ◽  
pp. 1748-1756 ◽  
Author(s):  
Sarra Boudriga ◽  
Besma Elmhawech ◽  
Askri Moheddine
Keyword(s):  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Diastereoselective Synthesis

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.

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.

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

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.

Reactions of 4-Pyrones with Azomethine Ylides as a Chemo­selective Method for the Construction of Multisubstituted Pyrano[2,3-c]pyrrolidines

Synthesis ◽  
2021 ◽  
Author(s):  
Dmitrii L. Obydennov ◽  
Vyacheslav D. Steben’kov ◽  
Konstantin L. Obydennov ◽  
Sergey A. Usachev ◽  
Vladimir S. Moshkin ◽  
...  
Keyword(s):  
Double Bond ◽  
Ring Opening ◽  
Azomethine Ylides ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
Computational Studies ◽  
Carbon Double Bond ◽  
Reactivity Indexes ◽  
Reaction Proceeds

Abstract4-Pyrones bearing electron-donating and electron-withdrawing groups react with nonstabilized azomethine ylides to form pyrano[2,3-c]pyrrolidines in moderate to good yields. The reaction proceeds chemoselectively as a 1,3-dipolar cycloaddition of the azomethine ylide at the carbon–carbon double bond of the pyrone activated by the electron-withdrawing substituent. The reactivity of 4-pyrones toward azomethine ylides was rationalized by computational studies with the use of reactivity indexes. The pyrano[2,3-c]pyrrolidine moiety could be modified, for example by a ring-opening transformation under the action of hydrazine to provide pyrazolyl-substituted pyrrolidines.

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