ChemInform Abstract: 2,5-Unsubstituted Pyrrolidines from Formaldehyde and Amino Acids Through in situ Azomethine-Ylide 1,3-Dipolar Cycloaddition to Alkenes.

1986 ◽  
Vol 17 (16) ◽  
Author(s):  
M. JOUCLA ◽  
J. MORTIER
Keyword(s):  
Amino Acids ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition

Cross 1,3-dipolar cycloadditions of C,N-cyclic azomethine imines with an N-benzyl azomethine ylide: facile access to fused tricyclic 1,2,4-hexahydrotriazines

2019 ◽  
Vol 17 (2) ◽  
pp. 244-247 ◽  
Author(s):  
Kai-Kai Wang ◽  
Yan-Li Li ◽  
Zhan-Yong Wang ◽  
Meng-Wei Hu ◽  
Ting-Ting Qiu ◽  
...  
Keyword(s):  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
Dipolar Cycloadditions ◽  
Azomethine Imines

A cross 1,3-dipolar cycloaddition of two different ylides between C,N-cyclic azomethine imines with an in situ generated non-stabilized azomethine ylide from an N-benzyl precursor is reported.

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.

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.

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...

scholarly journals Synthesis of Dispiro[Indeno[1,2-b]Quinoxaline-11,3′-Pyrrolizine-2′,2″-[1,3] Thiazolo[3,2-a]Pyrimidine Via Cycloaddition Reactions

2018 ◽  
Vol 42 (9) ◽  
pp. 453-455 ◽  
Author(s):  
Demin Ren ◽  
Xiaolian Hu ◽  
Yulin Huang ◽  
Xiaofang Li
Keyword(s):  
Cycloaddition Reaction ◽  
Crystallographic Analysis ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
X Ray

The 1,3-dipolar cycloaddition reaction of ethyl 5-aryl-2-(2-methoxy-2-oxoethylidene)-7-methyl-3-oxo-2,3-dihydro-5 H-[1,3]thiazolo[3,2- a] pyrimidine-6-carboxylate and azomethine ylide, which was generated in situ by the reaction of 11 H-indeno[1,2- b]quinoxalin-11-one and L-proline, afforded novel 6″ethyl 1′-methyl 5″aryl-7″methyl-3″oxo-5’,6’,7’,7a′-tetrahydro-1' H,3″ H,5″ H-dispiro[indeno[1,2- b]quinoxaline-11, 3 ‘-pyrrolizine-2’,2″-[1,3]thiazolo[3,2- a]pyrimidine-1’,6″-dicarboxylates in good yields. The structures of all the products were characterised thoroughly by NMR, IR and HRMS together with X-ray crystallographic analysis.

Synthesis of novel dispiro[indazole-5,3′-pyrrolidine-2′,3″-indole] derivatives via 1,3-dipolar cycloaddition of azomethine ylide

2017 ◽  
Vol 41 (7) ◽  
pp. 427-429
Author(s):  
Demin Ren ◽  
Guoqiang Kuang ◽  
Xiaolian Hu ◽  
Xiaofang Li
Keyword(s):  
Crystallographic Analysis ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
Indole Derivatives ◽  
X Ray

The 1,3-dipolar cycloaddition of azomethine ylide, generated in situ from isatin and sarcosine, to 5-arylmethylidene-1-phenyl-6,7-dihydro-1 H-indazol-4(5 H)-ones afforded novel 1′-methyl-4′-aryl-1-phenyl-6,7-dihydrodispiro[indazole-5,3′-pyrrolidine-2′,3″-indole]-2″,4(1 H,1″ H)-diones in moderate yields. The structures of all the products were characterised thoroughly by NMR, IR, HRMS, together with X-ray crystallographic analysis.

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.

Synthesis of Spiro[Pyrrolo[2,1-b][1,3]Benzothiazole-3,2′-[1,3]Thiazolo[3,2-a] Pyrimidine] via Cycloaddition Reactions

2018 ◽  
Vol 42 (5) ◽  
pp. 260-263 ◽  
Author(s):  
Qing Zeng ◽  
Demin Ren ◽  
Xingliang Fu ◽  
Xiaofang Li
Keyword(s):  
Cycloaddition Reaction ◽  
Crystallographic Analysis ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
X Ray

The 1,3-dipolar cycloaddition reaction of ethyl-5-aryl-2-[( Z)-2-methoxy-2-oxoethylidene]-7-methyl-3-oxo-3,5-dihydro-2 H-thiazolo[3,2- a] pyrimidine-6-carboxylates and azomethine ylide, which was generated in situ by the reaction of N-4-methoxyphenacylbenzothiazolium bromides and triethylamine, yielded novel 6′-ethyl-2-methyl-5′-aryl-1-(4-methoxybenzoyl)-7-methyl-3′-oxo-1,2-dihydro-5 H-spiro[pyrrolo[2,1- b][1,3]benzothiazole-3,2′-[1,3]thiazolo[3,2- a]pyrimidine]-2,6′-dicarboxylates in moderate yields. The structures of all of the products were characterised by NMR, IR, HRMS spectrometry, together with X-ray crystallographic analysis.

scholarly journals Regioselective Synthesis of Dispiro Pyrrolizidines as Potent Antimicrobial Agents for Human Pathogens

2013 ◽  
Vol 2013 ◽  
pp. 1-8 ◽  
Author(s):  
N. Sirisha ◽  
R. Raghunathan
Keyword(s):  
Amino Acids ◽  
Antibacterial Activity ◽  
Antimicrobial Agents ◽  
Cycloaddition Reaction ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
Human Pathogens ◽  
Synthetic Compounds ◽  
Good Antibacterial Activity ◽  
Secondary Amino

Synthesis of a series of novel dispiro pyrrolizidines has been accomplished by 1,3-dipolar cycloaddition reaction of azomethine ylide generated from secondary amino acids and diketones with bischalcones. These compounds were evaluated for their antibacterial activity. Most of the synthetic compounds exhibited good antibacterial activity against microorganisms.

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