1,3-Dipolar cycloadditions of ylide of 5-nitro-2-furfurylpyridinium bromide in indolizine synthesis

1982 ◽  
Vol 47 (6) ◽  
pp. 1738-1745 ◽  
Author(s):  
Jarmila Štetinová ◽  
Miloslava Dandárová ◽  
Jaroslav Kováč ◽  
Darina Mesárošová ◽  
Ján Leško
Keyword(s):  
Mass Spectra ◽  
Cycloaddition Reaction ◽  
Ethyl Acrylate ◽  
Dipolar Cycloaddition ◽  
Dimethyl Acetylenedicarboxylate ◽  
Diethyl Maleate ◽  
Dipolar Cycloadditions ◽  
H Nmr

Substituted 3-(5-nitro-2-furyl)indolizines III-X were synthesized by 1,3-dipolar cycloaddition reaction of the ylide II, generated from 5-nitro-2-furfurylpyridinium bromide (I), with acrylonitrile, ethyl acrylate, diethyl maleate, benzalacetophenone, ethyl 3-(5-nitro-2-furyl)acrylate, (5-nitro-2-furfurylidene)acetophenone, β-nitrostyrene and dimethyl acetylenedicarboxylate. The structure of these products is discussed on the basis of their 1H NMR and mass spectra.

scholarly journals Huisgen [3 + 2] Dipolar Cycloadditions of Phthalazinium Ylides to Activated Symmetric and Non-Symmetric Alkynes

Molecules ◽  
2020 ◽  
Vol 25 (19) ◽  
pp. 4416
Author(s):  
Vasilichia Antoci ◽  
Costel Moldoveanu ◽  
Ramona Danac ◽  
Violeta Mangalagiu ◽  
Gheorghita Zbancioc
Keyword(s):  
Reaction Time ◽  
Comparative Study ◽  
Cycloaddition Reaction ◽  
Environmentally Friendly ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Dimethyl Acetylenedicarboxylate ◽  
Thermal Heating ◽  
Dipolar Cycloadditions ◽  
Methyl Propiolate

We present herein a straightforward and efficient pathway for the synthesis of pyrrolophthalazine cycloadducts via Huisgen [3 + 2] dipolar cycloaddition reactions of phthalazinium ylides to methyl propiolate or dimethyl acetylenedicarboxylate (DMAD). A thoroughly comparative study concerning the efficiency of synthesis, conventional thermal heating (TH) versus microwave (MW) and ultrasound (US) irradiation, has been performed. The cycloaddition reactions of phthalazinium ylides to methyl propiolate occur regiospecific, with a single regioisomer being obtained. Under conventional TH, the cycloaddition reaction of phthalazinium ylides with DMAD occurs to a mixture of inseparable partial and fully aromatized pyrrolophthalazine cycloadducts, while MW or US irradiation are leading only to fully aromatized compounds, with the reactions becoming selective. A feasible mechanism for formation of fully aromatized compounds is presented. Besides selectivity, it has to be noticed that the reaction setup under MW or US irradiation offer a number of other certain advantages: higher yields, decreasing of the amount of used solvent comparative with TH, decreasing of the reaction time from hours to minutes and decreasing of the consumed energy; consequently, these reactions could be considered environmentally friendly.

scholarly journals Introduction of an isoxazoline unit to the β-position of porphyrin via regioselective 1,3-dipolar cycloaddition reaction

2019 ◽  
Vol 15 ◽  
pp. 1434-1440
Author(s):  
Xiujun Liu ◽  
Xiang Ma ◽  
Yaqing Feng
Keyword(s):  
Crystal Structure ◽  
Carbonyl Group ◽  
Mass Spectra ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Steric Interaction ◽  
Dimeric Complex ◽  
Nitrile Oxides ◽  
H Nmr ◽  
Basic Features

Isoxazoline-linked porphyrins have been synthesized by a regioselective 1,3-dipolar cycloaddition reaction between vinylporphyrin 2 and nitrile oxides. The steric interaction directed the reaction trajectory, in which only the product with a link between the 5-position of the isoxazoline and the β-position of porphyrin was observed. The isoxazoline-porphyrins 3a,b have been characterized by absorption, emission, 1H NMR and mass spectra. Later, the crystal structure of 3a was obtained and confirmed the basic features of the NMR-derived structure. Furthermore, a pair of enantiomers of 3a presented in the crystal, which formed a dimeric complex through intermolecular coordination between the Zn2+ center and the carbonyl group of the second molecule.

1,3-Dipolar Cycloaddition Reaction of Dimethyl Acetylenedicarboxylate with Hydrazones

Heterocycles ◽  
1974 ◽  
Vol 2 (2) ◽  
pp. 280 ◽  
Author(s):  
Haruo Ogura ◽  
Hiroshi Takahashi ◽  
Kazuo Kubo ◽  
Kozo Ogawa ◽  
Hitomi Sakai
Keyword(s):  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Dimethyl Acetylenedicarboxylate

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.

Beyond the Alternatives that Switch the Mechanism of the 1,3-Dipolar CyCloadditions from Concerted to Stepwise or Vice Versa: A Literature Review

2016 ◽  
Vol 41 (4) ◽  
pp. 331-344 ◽  
Author(s):  
Seyyed Amir Siadati
Keyword(s):  
Organic Chemistry ◽  
Literature Review ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Stepwise Mechanism ◽  
Dipolar Cycloadditions ◽  
Catalyst Free ◽  
Number Of Factors ◽  
Reaction Channels ◽  
The 1960S

For several decades, the concerted or stepwise character of the mechanism of the 1,3-dipolar cycloaddition reaction has been one of the most debated issues in the field of organic chemistry. The significance of this problem is due to the fact that in a catalyst-free 1,3-dipolar cycloaddition, when the mechanism switches from concerted to stepwise, the stereospecificity is lost and thus unwanted stereoisomers may emerge. The first proposals about the mechanism of the 1,3-dipolar reaction were due to Huisgen (concerted model) and subsequently by Firestone (two-step diradical channel) in the 1960s. After a decade of debate, most researchers accepted the concerted model for the reaction, but during these years, researchers reported some examples of the stepwise mechanism for catalyst-free 1,3-dipolar cycloadditions. This review attempts to find a number of factors that could influence the reaction channels and switch the mechanism from concerted to stepwise, or vice versa.

scholarly journals Synthesis, ADMET and Docking Studies of Novel Pyrazoles Incorporating Coumarin Moiety as Tyrosine Kinase (Src) Inhibitors

2021 ◽  
Vol 11 (5) ◽  
pp. 13706-13714
Keyword(s):  
Tyrosine Kinase ◽  
Mass Spectra ◽  
Kinase Inhibitors ◽  
Cycloaddition Reaction ◽  
Docking Studies ◽  
Dipolar Cycloaddition ◽  
Inhibition Activity ◽  
Spectral Techniques ◽  
Chemical Structures

Novel pyrazoles incorporating coumarin moiety have been synthesized by the 1,3-dipolar cycloaddition reaction of the nitrilimines that were generated in situ from hydrazonyl halides by the action of triethylamine and the enaminone named E-3-(3-(dimethylamino)acryloyl)-8-methoxy-2H-chromen-2-one (1) in dry benzene for 6 h. These novel compounds' chemical structures were elucidated by physical and spectral techniques, including FTIR, 1H-NMR, 13C-NMR, 1H-13C HMBC NMR, and mass spectra. These molecules were predicted to show tyrosine kinase inhibition activity, which was further validated by docking studies. These molecules also showed good ADMET properties and passed Lipinski’s filters for drug-likeness. These results collectively paved the way for developing pyrazoles incorporating coumarin moiety as possible tyrosine kinase inhibitors.

1,3-Dipolar Cycloadditions Involving Allenes: Synthesis of Five-Membered Rings

2020 ◽  
Vol 23 (27) ◽  
pp. 3064-3134 ◽  
Author(s):  
Ana L. Cardoso ◽  
Maria I.L. Soares
Keyword(s):  
Transition Metal ◽  
Cycloaddition Reaction ◽  
Building Blocks ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Relevant Research ◽  
Dipolar Cycloadditions ◽  
Recent Developments ◽  
Synthetic Equivalent ◽  
Metal Catalyzed

The 1,3-dipolar cycloaddition reaction is a powerful and versatile strategy for the synthesis of carbocyclic and heterocyclic five-membered rings. Herein, the most recent developments on the [3+2] cycloaddition reactions using allenes acting either as dipolarophiles or 1,3-dipole precursors, are highlighted. The recent contributions on the phosphine- and transition metal-catalyzed [3+2] annulations involving allenes as substrates are also covered, with the exception of those in which the formation of a 1,3-dipole (or synthetic equivalent) is not invoked. This review summarizes the most relevant research in which allenes are used as building blocks for the construction of structurally diverse five-membered rings via [3+2] annulation reactions.

Highly enantioselective catalytic 1,3-dipolar cycloadditions of α-alkyl diazoacetates: efficient synthesis of functionalized 2-pyrazolines

2015 ◽  
Vol 13 (9) ◽  
pp. 2745-2749 ◽  
Author(s):  
Sung Il Lee ◽  
Ka Eun Kim ◽  
Geum-Sook Hwang ◽  
Do Hyun Ryu
Keyword(s):  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Efficient Synthesis ◽  
Dipolar Cycloadditions

Chiral oxazaborolidinium ion catalyzed 1,3-dipolar cycloaddition reaction of α-substituted diazoacetates gives functionalized 2-pyrazolines in high to excellent enantiomeric ratios.

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