scholarly journals Studies toward Total Synthesis of (±)-Caldaphnidine C via One-Pot Sequential Intramolecular Vilsmeier–Haack and Azomethine Ylide 1,3-Dipolar Cycloaddition

2016 ◽  
Vol 81 (19) ◽  
pp. 9247-9268 ◽  
Author(s):  
Jonathan Boudreault ◽  
François Lévesque ◽  
Guillaume Bélanger
Keyword(s):  
Total Synthesis ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
One Pot

Concise Synthesis of Tryptanthrin Spiro Analogues with In Vitro Antitumor Activity Based on One-Pot, Three-Component 1,3-Dipolar Cycloaddition of Azomethine Ylides to Сyclopropenes

Synthesis ◽  
2018 ◽  
Vol 51 (03) ◽  
pp. 713-729 ◽  
Author(s):  
Vitali Boitsov ◽  
Alexander Stepakov ◽  
Alexander Filatov ◽  
Nickolay Knyazev ◽  
Stanislav Shmakov ◽  
...  
Keyword(s):  
Antitumor Activity ◽  
Azomethine Ylides ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
One Pot ◽  
Economic Method ◽  
Reaction Proceeds ◽  
High Yields

A simple, efficient and atom-economic method has been developed for the synthesis of complex alkaloid-like compounds with spiro-fused indolo[2,1-b]quinazoline and cyclopropa[a]pyrrolizine or 3-azabicyclo[3.1.0]hexane moieties. We have found that one-pot, three-component 1,3-dipolar cycloaddition reactions allow the desired products to be obtained from various cyclopropene derivatives with tryptanthrin-derived azomethine ylides generated in situ, in good to high yields and excellent diastereoselectivity. The possibility of ylide generation was exemplified by using α-amino acids (l-proline, l-4-thiazolidincarboxylic acid) and simplest peptides (dipeptide Gly-Gly, tripeptide Gly-Gly-Gly). Quantum chemical investigations indicate that the reaction proceeds through the S-shaped azomethine ylide, the interaction of which with cyclopropenes proceeds via a less sterically hindered endo-transition state. The antitumor activity of some of spiro-tryptanthrin derivatives against erythroleukemia (K562), cervical carcinoma (HeLa) and colon carcinoma (CT26) cell lines was evaluated in vitro by MTS-assay.

One-pot highly diastereoselective synthesis of some novel spiro pyrrolizidines via 1,3-dipolar cycloaddition reaction of azomethine ylide

2004 ◽  
Vol 2004 (5) ◽  
pp. 347-349 ◽  
Author(s):  
Javad Azizian ◽  
R. Dastkhan ◽  
Ali A. Mohammadi ◽  
Mohammad R. Mohammadizadeh ◽  
Keyword(s):  
Cycloaddition Reaction ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
Diastereoselective Synthesis ◽  
One Pot

scholarly journals Unexpected one-pot formation of the 1H-6a,8a-epiminotricyclopenta[a,c,e][8]annulene system from cyclopentanone, ammonia and dimethyl fumarate. Synthesis of highly strained polycyclic nitroxide and EPR study

2019 ◽  
Vol 15 ◽  
pp. 2664-2670
Author(s):  
Sergey A Dobrynin ◽  
Igor A Kirilyuk ◽  
Yuri V Gatilov ◽  
Andrey A Kuzhelev ◽  
Olesya A Krumkacheva ◽  
...  
Keyword(s):  
Spin Relaxation ◽  
Ammonium Acetate ◽  
Dimethyl Fumarate ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
One Pot ◽  
Unexpected Formation ◽  
Highly Strained ◽  
Multistep Reaction

The unexpected formation of a highly strained polycyclic amine was observed in a one-pot synthesis from cyclopentanone, dimethyl fumarate and ammonium acetate. This multistep reaction includes 1,3-dipolar cycloaddition of dimethyl fumarate to the cyclic azomethine ylide formed in situ from cyclopentanone and ammonia. The polycyclic amine product was easily converted into a sterically shielded polycyclic nitroxide. The EPR spectra and spin relaxation behavior of the nitroxide were studied in solution. The spin relaxation seems well suited for the use as a biological spin label and are comparable with those of cyclic nitroxides with two spirocyclic moieties adjacent to the N–O · group.

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