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...

scholarly journals A Novel Three-Component Reaction for the Diastereoselective Synthesis of 2H-Pyrimido[2,1-a]isoquinolines via 1,4-Dipolar Cycloaddition.

ChemInform ◽  
2003 ◽  
Vol 34 (10) ◽  
Author(s):  
Vijay Nair ◽  
A. R. Sreekanth ◽  
N. Abhilash ◽  
Mohan M. Bhadbhade ◽  
Rajesh C. Gonnade
Keyword(s):  
Dipolar Cycloaddition ◽  
Diastereoselective Synthesis ◽  
Three Component Reaction

Regio- and Diastereoselective Synthesis of Novel Polycyclic Pyrrolo[2,1-a]isoquinolines Bearing Indeno[1,2-b]quinoxaline Moieties by a Three-Component [3+2]-Cycloaddition Reaction

Synlett ◽  
2019 ◽  
Vol 31 (03) ◽  
pp. 267-271 ◽  
Author(s):  
Firouz Matloubi Moghaddam ◽  
Atiyeh Moafi ◽  
Behzad Jafari ◽  
Alexander Vilinger ◽  
Peter Langer
Keyword(s):  
Cycloaddition Reaction ◽  
Reaction Times ◽  
Dipolar Cycloaddition ◽  
Diastereoselective Synthesis ◽  
X Ray Diffraction ◽  
Reaction Conditions ◽  
One Pot ◽  
Three Component Reaction ◽  
Relative Stereochemistry ◽  
High Yields

A regio- and diastereoselective synthesis of 2,3-dihydro-10b′H-spiro[indeno[1,2-b]quinoxaline-11,1′-pyrrolo[2,1-a]isoquinoline]-2′,3′-diylbis(phenylmethanone) derivatives containing four contiguous chiral stereocenters was achieved through 1,3-dipolar cycloaddition of isoquinolinium N-ylides in a one-pot three-component reaction. The desired products were obtained in short reaction times and in moderate to high yields (up to 92%) under relatively mild reaction conditions. The structure and relative stereochemistry of the desired product was confirmed by X-ray diffraction analysis.

A Novel Three-Component Reaction for the Diastereoselective Synthesis of 2H-Pyrimido[2,1-a]isoquinolines via 1,4-Dipolar Cycloaddition†

2002 ◽  
Vol 4 (21) ◽  
pp. 3575-3577 ◽  
Author(s):  
Vijay Nair ◽  
A. R. Sreekanth ◽  
N. Abhilash ◽  
Mohan M. Bhadbhade ◽  
Rajesh C. Gonnade
Keyword(s):  
Dipolar Cycloaddition ◽  
Diastereoselective Synthesis ◽  
Three Component Reaction

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.

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