ChemInform Abstract: THE 1,3-DIPOLAR CYCLOADDITION REACTION OF FERVENULIN 4-OXIDES WITH DIMETHYL ACETYLENEDICARBOXYLATE, A NOVEL SYNTHESIS OF PYRROLO(3,2-D)PYRIMIDINES (9-DEAZAPURINES)

1978 ◽  
Vol 9 (48) ◽  
Author(s):  
K. SENGA ◽  
M. ICHIBA ◽  
S. NISHIGAKI
Keyword(s):  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Dimethyl Acetylenedicarboxylate ◽  
Novel Synthesis

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

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.

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.

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