scholarly journals The regioselective synthesis of spirooxindolo pyrrolidines and pyrrolizidines via three-component reactions of acrylamides and aroylacrylic acids with isatins and α-amino acids

2014 ◽  
Vol 10 ◽  
pp. 117-126 ◽  
Author(s):  
Tatyana L Pavlovskaya ◽  
Fedor G Yaremenko ◽  
Victoria V Lipson ◽  
Svetlana V Shishkina ◽  
Oleg V Shishkin ◽  
...  
Keyword(s):  
Amino Acids ◽  
Carboxylic Acids ◽  
Regioselective Synthesis ◽  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
One Pot

The regioselective three-component condensation of azomethine ylides derived from isatins and α-amino acids with acrylamides or aroylacrylic acids as dipolarophiles has been realized through a one-pot 1,3-dipolar cycloaddition protocol. Decarboxylation of 2'-aroyl-2-oxo-1,1',2,2',5',6',7',7a'-octahydrospiro[indole-3,3'-pyrrolizine]-1'-carboxylic acids is accompanied by cyclative rearrangement with formation of dihydropyrrolizinyl indolones.

scholarly journals Multicomponent synthesis of spiropyrrolidine analogues derived from vinylindole/indazole by a 1,3-dipolar cycloaddition reaction

2016 ◽  
Vol 12 ◽  
pp. 2893-2897 ◽  
Author(s):  
Manjunatha Narayanarao ◽  
Lokesh Koodlur ◽  
Vijayakumar G Revanasiddappa ◽  
Subramanya Gopal ◽  
Susmita Kamila
Keyword(s):  
Amino Acids ◽  
Cycloaddition Reaction ◽  
Thermal Conditions ◽  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Side Chains ◽  
Multicomponent Synthesis ◽  
One Pot ◽  
Cyclic Adducts

A new series of spiropyrrolidine compounds containing indole/indazole moieties as side chains have been accomplished via a one-pot multicomponent synthesis. The method uses the 1,3-dipolar cycloaddition reaction between N-alkylvinylindole/indazole and azomethine ylides, prepared in situ from cyclic/acyclic amino acids. The 1,3-dipolar cycloaddition proceeds efficiently under thermal conditions to afford the regio- and stereospecific cyclic adducts.

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.

A highly diastereoselective one-pot three-component 1,3-dipolar cycloaddition of cyclopropenes with azomethine ylides generated from 11H-indeno[1,2-b]-quinoxalin-11-ones

2018 ◽  
Vol 5 (4) ◽  
pp. 595-605 ◽  
Author(s):  
A. S. Filatov ◽  
N. A. Knyazev ◽  
M. N. Ryazantsev ◽  
V. V. Suslonov ◽  
A. G. Larina ◽  
...  
Keyword(s):  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Efficient Synthesis ◽  
One Pot

A simple and efficient synthesis of compounds with spiro-fused 11H-indeno[1,2-b]quinoxaline and azabicyclo[3.1.0]hexane or cyclopropa[a]pyrrolizine moieties was developed.

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 An efficient and facile access to highly functionalized pyrrole derivatives

2018 ◽  
Vol 14 ◽  
pp. 884-890 ◽  
Author(s):  
Meng Gao ◽  
Wenting Zhao ◽  
Hongyi Zhao ◽  
Ziyun Lin ◽  
Dongfeng Zhang ◽  
...  
Keyword(s):  
Medicinal Chemistry ◽  
Alcohol Solution ◽  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Complete Oxidation ◽  
One Pot ◽  
Pyrrole Derivatives ◽  
Chemistry Research ◽  
Efficient Construction ◽  
Sodium Alkoxide

A straightforward and one-pot synthesis of pyrrolo[3,4-c]pyrrole-1,3-diones via Ag(I)-catalyzed 1,3-dipolar cycloaddition of azomethine ylides with N-alkyl maleimide, followed by readily complete oxidation with DDQ, has been successfully developed. Further transformation with alkylamine/sodium alkoxide alcohol solution conveniently afforded novel polysubstituted pyrroles in good to excellent yields. This methodology for highly functionalized pyrroles performed well over a broad scope of substrates. It is conceivable that this efficient construction method for privileged pyrrole scaffolds could deliver more active compounds for medicinal chemistry research.

A One-Pot Synthesis of Highly Functionalized Indolizines by 1,3-Dipolar Cycloaddition of Azomethine Ylides and Phosphorylated Hydroxyketenimines

Synlett ◽  
2016 ◽  
Vol 27 (18) ◽  
pp. 2601-2605 ◽  
Author(s):  
Issa Yavari ◽  
Maryam Naeimabadi ◽  
Reza Hosseinpour ◽  
Mohammad Halvagar
Keyword(s):  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
One Pot ◽  
One Pot Synthesis

scholarly journals Regioselective synthesis of fullerene multiadducts via tether-directed 1,3-dipolar cycloaddition

2015 ◽  
Vol 13 (42) ◽  
pp. 10505-10510 ◽  
Author(s):  
Bolong Zhang ◽  
Jonathan M. White ◽  
David J. Jones ◽  
Wallace W. H. Wong
Keyword(s):  
Amino Acid ◽  
Regioselective Synthesis ◽  
Dipolar Cycloaddition ◽  
One Pot

A class of fullerene bisadducts was synthesized in one-pot over two steps with regioselectivity using tether-directed functionalization approach. In extending this class of materials, interesting variations in regioselectivity was observed when different amino acid reactants were used.

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