scholarly journals Synthesis of diversely substituted bis-pyrrolizidino/ thiopyrrolizidino oxindolo/acenaphthyleno curcuminoids via sequential azomethine ylide cycloaddition

RSC Advances ◽  
2018 ◽  
Vol 8 (34) ◽  
pp. 18938-18951 ◽  
Author(s):  
Meenakshi Singh ◽  
Abhijit Hazra ◽  
Yogesh P. Bharitkar ◽  
Ritu Kalia ◽  
Ashutosh Sahoo ◽  
...  
Keyword(s):  
Cycloaddition Reaction ◽  
Azomethine Ylide

Curcumin has been transformed to several diversely substituted bis-pyrrolizidino/thiopyrrolizidino oxindolo/acenaphthyleno curcuminoids via a sequential azomethine ylide cycloaddition reaction.

How the mechanism of a [3 + 2] cycloaddition reaction involving a stabilized N-lithiated azomethine ylide toward a π-deficient alkene is changed to stepwise by solvent polarity? What is the origin of its regio- and endo stereospecificity? A DFT study using NBO, QTAIM, and NCI analyses

RSC Advances ◽  
2016 ◽  
Vol 6 (79) ◽  
pp. 75299-75314 ◽  
Author(s):  
Saeedreza Emamian
Keyword(s):  
Cycloaddition Reaction ◽  
Solvent Polarity ◽  
Dft Study ◽  
Azomethine Ylide

The regio- and endo stereospecific 32CA reaction of the stabilized N-lithiated azomethine ylide 2 toward the π-deficient alkene 3in THF occurs to afford cycloadduct 6via a stepwise mechanism, passing through the zwitterionic intermediate 4.

Stepwise π-extension of meso-alkylidenyl porphyrins through sequential 1,3-dipolar cycloaddition and redox reactions

2014 ◽  
Vol 50 (66) ◽  
pp. 9277-9280 ◽  
Author(s):  
Dowoo Park ◽  
Seung Doo Jeong ◽  
Masatoshi Ishida ◽  
Chang-Hee Lee
Keyword(s):  
Redox Reactions ◽  
Cycloaddition Reaction ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
High Yields

Novel pi-extended,meso-malonylidene porphyrins have been synthesized in high yields by 1,3-dipolar cycloaddition reaction with the azomethine ylide.

scholarly journals Synthesis and Biological Evaluation of S-, O- and Se-Containing Dispirooxindoles

Molecules ◽  
2021 ◽  
Vol 26 (24) ◽  
pp. 7645
Author(s):  
Maksim Kukushkin ◽  
Vladimir Novotortsev ◽  
Vadim Filatov ◽  
Yan Ivanenkov ◽  
Dmitry Skvortsov ◽  
...  
Keyword(s):  
Cell Line ◽  
Computational Study ◽  
Cycloaddition Reaction ◽  
Biological Evaluation ◽  
Azomethine Ylide ◽  
Prostate Cell ◽  
In Silico Study ◽  
P53 Activation ◽  
Synthesis And Biological Evaluation

A series of novel S-, O- and Se-containing dispirooxindole derivatives has been synthesized using 1,3-dipolar cycloaddition reaction of azomethine ylide generated from isatines and sarcosine at the double C=C bond of 5-indolidene-2-chalcogen-imidazolones (chalcogen was oxygen, sulfur or selenium). The cytotoxicity of these dispiro derivatives was evaluated in vitro using different tumor cell lines. Several molecules have demonstrated a considerable cytotoxicity against the panel and showed good selectivity towards colorectal carcinoma HCT116 p53+/+ over HCT116 p53−/− cells. In particular, good results have been obtained for LNCaP prostate cell line. The performed in silico study has revealed MDM2/p53 interaction as one of the possible targets for the synthesized molecules. However, in contrast to selectivity revealed during the cell-based evaluation and the results obtained in computational study, no significant p53 activation using a reporter construction in p53wt A549 cell line was observed in a relevant concentration range.

scholarly journals Diastereoselective Synthesis of Spiro[Pyrrolo[2,1-B][1,3] Benzothiazole-3,5′-[1,3]Thiazolo[3,2-B][1,2,4]Triazol]-6′-Ones via Cycloaddition Reaction of Benzothiazolium Salts

2018 ◽  
Vol 42 (7) ◽  
pp. 371-373 ◽  
Author(s):  
Qing Zeng ◽  
Demin Ren ◽  
Yulin Huang ◽  
Xinliang Fu ◽  
Xiaofang Li
Keyword(s):  
Cycloaddition Reaction ◽  
Crystallographic Analysis ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
Diastereoselective Synthesis ◽  
X Ray

The 1,3-dipolar cycloaddition reaction of (Z)-5-arylidene[1,3]thiazolo[3,2-b][1,2,4]triazol-6(5H)-one and azomethine ylide, which was generated in situ by the reaction of N-4-methoxyphenacylbenzothiazolium bromides and triethylamine, afforded novel 2-(aryl)-1-(4-methoxybenzoyl)-1,2-dihydrospiro[pyrrolo[2,1-b][1,3]benzothiazole-3,5′-[1,3]thiazolo[3,2-b][1,2,4]triazol]-6′-ones in moderate yields. The structures of all the products were characterised thoroughly by NMR, IR and HRMS spectroscopy together with X-ray crystallographic analysis.

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