Cycloaddition Reaction of Vinylphenylfurans and Dimethyl Acetylenedicarboxylate to [8 + 2] Isomers via Tandem [4 + 2]/Diradical Alkene–Alkene Coupling/[1,3]-H Shift Reactions: Experimental Exploration and DFT Understanding of Reaction Mechanisms

2016 ◽  
Vol 81 (18) ◽  
pp. 8155-8168 ◽  
Author(s):  
Kai Chen ◽  
Feng Wu ◽  
Lijuan Ye ◽  
Zi-You Tian ◽  
Zhi-Xiang Yu ◽  
...  
Keyword(s):  
Reaction Mechanisms ◽  
Cycloaddition Reaction ◽  
Dimethyl Acetylenedicarboxylate

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.

scholarly journals Activated lactams. VI. The cycloaddition reaction of cyclic ketene-S,N-acetals with dimethyl acetylenedicarboxylate.

1982 ◽  
Vol 30 (11) ◽  
pp. 3959-3964 ◽  
Author(s):  
HIROKI TAKAHATA ◽  
AKIRA TOMIGUCHI ◽  
ATSUSHI HAGIWARA ◽  
TAKAO YAMAZAKI
Keyword(s):  
Cycloaddition Reaction ◽  
Dimethyl Acetylenedicarboxylate

DFT study on reaction mechanisms of propylamine and dimethyl acetylenedicarboxylate with 1,3-dimethylalloxan

2013 ◽  
Vol 1004 ◽  
pp. 47-55 ◽  
Author(s):  
Yanyan Zhu ◽  
Yunxia Li ◽  
Wenjing Zhang ◽  
Qilin Zhao ◽  
Mingsheng Tang
Keyword(s):  
Reaction Mechanisms ◽  
Dft Study ◽  
Dimethyl Acetylenedicarboxylate
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