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.

scholarly journals Synthesis of pyrrolizidines and indolizidines by multicomponent 1,3-dipolar cycloaddition of azomethine ylides

2019 ◽  
Vol 91 (4) ◽  
pp. 575-596 ◽  
Author(s):  
Carmen Nájera ◽  
José Miguel Sansano
Keyword(s):  
Amino Acid ◽  
Azomethine Ylides ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
Amino Acid Derivatives ◽  
Reaction Conditions ◽  
Dipolar Cycloadditions ◽  
Spiro Derivatives ◽  
Stabilized Azomethine Ylides

Abstract Different multicomponent 1,3-dipolar cycloadditions (1,3-DC) of cyclic α-amino acid derivatives with aldehydes and dipolarophiles have been described as efficient and simple methodologies for the synthesis of the pyrrolidine unit of pyrrolizidines and indolizidines. When free cyclic α-amino acids are used, a thermal promoted decarboxylative process generates in situ the corresponding non-stabilized azomethine ylides, which afforded the corresponding pyrrolizidines and indolizidines with a hydrogen in the bicyclic units. This methodology has been employed to the synthesis of complex systems including spiro derivatives when ketones are used as carbonyl component. In addition, working with cyclic α-amino acid derived esters, the three-component 1,3-DC takes place under milder reaction conditions giving the corresponding pyrrolizidines and indolizidines with an alkoxycarbonyl group in the bridge adjacent carbon to the nitrogen. This methodology can be carried out by a double consecutive or stepwise 1,3-DC to provide pyrrolizidines via the precursor prolinates. The conformation of the azomethine ylide controls the endo/exo diastereoselectivity of the 1,3-DC.

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.

Corroles in 1,3-dipolar cycloaddition reactions

2009 ◽  
Vol 13 (03) ◽  
pp. 358-368 ◽  
Author(s):  
Luís S. H. P. Vale ◽  
Joana F. B. Barata ◽  
Carla I. M. Santos ◽  
Maria G. P. M. S. Neves ◽  
Maria A. F. Faustino ◽  
...  
Keyword(s):  
Single Crystal ◽  
Diffraction Analysis ◽  
Dimethyl Fumarate ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
Dimethyl Acetylenedicarboxylate ◽  
X Ray Diffraction ◽  
X Ray ◽  
Dipolar Cycloadditions ◽  
Pyridine Complex

The azomethine ylide generated from the reaction of a corrole-3-carbaldehyde and N-methylglycine was trapped with dimethyl fumarate, dimethyl acetylenedicarboxylate and fullerene C60 in 1,3-dipolar cycloadditions. A similar azomethine ylide generated from a corrole-2-carbaldehyde was trapped with 1,4-naphthoquinone, yielding the expected dehydrogenated 1,3-dipolar cycloadduct and a quinone-fused corrole derivative. A detailed synchrotron single-crystal X-ray diffraction analysis of the gallium(III)(pyridine) complex of 5,10,15-tris(pentafluorophenyl)corrole-3-carbaldehyde is also presented.

scholarly journals 1,3-Dipolar Cycloadditions of Isatin N,N′‑Cyclic Azomethine Imines with Alkynes for the synthesis of spiro[indoline-3,1'-pyrazolo[1,2-a]pyrazoles]

2019 ◽  
Author(s):  
Yang Shi ◽  
Gangqiang Wang ◽  
Zhiyu Chen ◽  
Minghu Wu ◽  
Jian Wang ◽  
...  
Keyword(s):  
Functional Group ◽  
Biologically Active ◽  
Dipolar Cycloaddition ◽  
Dipolar Cycloadditions ◽  
Azomethine Imine ◽  
Azomethine Imines

CuCO3 catalyzed 1, 3-dipolar cycloaddition of isatin N,N′‑cyclic azomethine imine has been developed.  Biologically active heterocyclic spiro[indoline-3,1'-pyrazolo[1,2-a]pyrazoles] were prepared as single regioisomers in good yields and functional group compatibility.

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...

1,3-Dipolar cycloadditions of N-(5-nitro-2-furfuryl)isoquinolinium bromide in the synthesis of benzoindolizines

1984 ◽  
Vol 49 (2) ◽  
pp. 533-542 ◽  
Author(s):  
Jarmila Štetinová ◽  
Jaroslav Kováč ◽  
František Považanec ◽  
Miloslava Dandárová ◽  
Alžbeta Pajchortová
Keyword(s):  
Dipolar Cycloaddition ◽  
Dipolar Cycloadditions ◽  
Spectral Evidence

Substituted 3-(5-nitro-2-furyl)benzo[g]indolizines III-XII were synthesized by a 1,3-dipolar cycloaddition of the ylide II formed in situ from N-(5-nitro-2-furfuryl)isoquinolinium bromide (I) and dimethyl butinedioate, diethyl butenedioate, 1-nitro-2-phenylethylene, ethyl 2-propenoate, ethyl 3-(5-nitro-2-furyl)-2-propenoate, 1,3-diphenyl-2-propenone, 1,3-diphenyl-2-propinone, 2-propenenitrile, 1-phenyl-3-(5-nitro-2-furyl)-2-propenone, and methyl 2-cyano-3-(4-nitrophenyl)-2-propenoate. Structure of these products was verified by spectral evidence.

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.

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