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 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.

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 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.

Ultrasound-Promoted Synthesis of Spirocyclopropanes from Switchable Starting Materials via Azomethine Ylide [3+2]-Cycloaddition

Synthesis ◽  
2021 ◽  
Author(s):  
Issa Yavari ◽  
Sara Sheikhi ◽  
Jamil Sheykhahmadi ◽  
Zohreh Taheri ◽  
Mohammad Reza Halvagar
Keyword(s):  
Single Crystal ◽  
Azomethine Ylides ◽  
Azomethine Ylide ◽  
X Ray ◽  
Green Protocol ◽  
Stereogenic Centers ◽  
Quinoxaline Derivatives ◽  
Excellent Selectivity

AbstractAn ultrasound-promoted green protocol to access a new series of spirocyclopropanes from indeno[1,2-b]quinoxaline derivatives and azomethine ylides, generated in situ from the iodine-catalyzed reaction of acetophenones as well as of 2-methylquinoline with pyridine in the presence of a base, is described. These transformations proceed via a spirocyclopropanation reaction followed by elimination of pyridine. Clear evidence for the structure of a spirocyclopropane-linked indenoquinoxaline derivative was obtained from single-crystal X-ray analysis. The most important feature of this reaction is the fact it forms three stereogenic centers, one of which is quaternary, with excellent selectivity.

Synthesis of Chromeno[3,4-c]Pyrazole from N-Tosylhydrazones and 3-Nitro-2-Phenyl-2H-Chromene

2017 ◽  
Vol 41 (12) ◽  
pp. 709-711 ◽  
Author(s):  
Xinliang Fu ◽  
Haotao Li ◽  
Demin Ren ◽  
Xiaofang Li
Keyword(s):  
Crystallographic Analysis ◽  
Dipolar Cycloaddition ◽  
X Ray

The intermolecular 1,3-dipolar cycloaddition of N-tosylhydrazones and 3-nitro-2-phenyl-2 H-chromene afforded 1-aryl-4-phenyl-2,4-dihydro-chromeno[3,4- c]pyrazoles in moderate to good yields. The structures of all the products were characterised by NMR, IR, HRMS and X-ray crystallographic analysis.

scholarly journals 10H-Pyrazino[2,3-b][1,4]benzotellurazine, a Novel Tellurium-Containing Heterocyclic System

2020 ◽  
Vol 2020 ◽  
pp. 1-5
Author(s):  
Diamond S. Smith ◽  
Dallas N. Alexis ◽  
Frank R. Fronczek ◽  
Thomas Junk
Keyword(s):  
Title Compound ◽  
Heterocyclic System ◽  
Crystallographic Analysis ◽  
Supramolecular Assemblies ◽  
Methyl Derivative ◽  
X Ray ◽  
Hydrogen Bonded

Condensation of 2,3-dichloropyrazine with 2-aminobenzenetellurole and 2-amino-5-methylbenzenetellurole, generated in situ by reduction of the corresponding ditellurides, resulted in the formation of novel 10H-pyrazino[2,3-b][1,4]benzotellurazine and its 7-methyl derivative. The products were purified via their well-crystallized 5,5-dibromo derivatives. X-ray crystallographic analysis of the title compound indicates that it has a pronounced V-shape and forms hydrogen-bonded dimers. Te, N-containing heterocycles have the potential of offering access to supramolecular assemblies.

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.

A Base-Promoted One-Pot Asymmetric Friedel–Crafts Alkylation/Michael Addition of 4-Substituted Indoles

Synthesis ◽  
2019 ◽  
Vol 52 (08) ◽  
pp. 1215-1222
Author(s):  
Robert Connon ◽  
Laura Carroll ◽  
Patrick J. Guiry
Keyword(s):  
Michael Addition ◽  
Crystallographic Analysis ◽  
Indole Derivatives ◽  
One Pot ◽  
X Ray ◽  
Excellent Yield ◽  
Tricyclic Core ◽  
Cyclobutane Derivative

Herein, we report a base-promoted Zn(II)–bis(oxazoline)-catalyzed one-pot Friedel–Crafts alkylation/Michael addition of 3-(indol-4-yl)acrylonitrile derivatives with trans-β-nitrostyrenes to yield the tricyclic core of the ergoline skeleton in up to 71% yield and 85% ee. During the purification of 3-(indol-4-yl)acrylonitrile, the key substrate for catalytic studies, a novel trans-cis-trans-cyclobutane derivative, thought to be formed via a [2+2] light-promoted cycloaddition, was identified by X-ray crystallographic analysis. Finally, a novel class of 4-substituted bis(indole)methane derivatives were serendipitously prepared in excellent yield by reacting 4-substituted indole derivatives with 4-nitrobenzaldehyde. One bis(indole)methane was characterized by X-ray crystallographic analysis.

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.

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