6972-69-6Relevant articles and documents
Palladium-Catalyzed Aminocarbonylation of Aryl Halides with N,N-Dialkylformamide Acetals
Hirata, Shuichi,Osako, Takao,Uozumi, Yasuhiro
, (2021/10/05)
We developed a protocol for the palladium-catalyzed aminocarbonylation of aryl halides using less-toxic formamide acetals as bench-stable aminocarbonyl sources under neutral conditions. Various aryl (including heteroaryl) halides reacted with N,N-dialkylformamide acetals in the presence of a catalytic amount of tris(dibenzylideneacetone)dipalladium(0)-chloroform adduct and xantphos to give the corresponding aromatic carboxamides at 90–140 °C without any activating agents or bases in up to quantitative chemical yield. This protocol was applied to aryl bromides, aryl iodides, and trifluoromethanesulfonic acid, as well as to relatively less-reactive aryl chlorides. A wide range of functionalities on the aromatic ring of the substrates were tolerated under the aminocarbonylation conditions. The catalytic aminocarbonylation was used to prepare the insect repellent N,N-diethyl-3-methylbenzamide as well as a synthetic intermediate of the dihydrofolate reductase inhibitor triazinate.
POCl3 promoted metal-free synthesis of tertiary amides by coupling of carboxylic acids and N,N-disubstituted formamides
Bi, Xiaojing,Li, Junchen,Shi, Enxue,Li, Yu,Liu, Ying,Wang, Hongmei,Xiao, Junhua
supporting information, p. 236 - 240 (2019/04/25)
Herein we report a robust and synthetically useful catalyst-free amination methodology by the coupling of carboxylic acids and N-substituted formamides using POCl3 as a promoter. Versatile amides with a wide array of substituent groups were prepared within only 1 h in good to excellent yields. And even multi-substituted aromatic carboxylic acids could give the desired products with satisfactory results.
Method for synthesizing phosphorus-oxychloride-promoted amide compound
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Paragraph 0095; 0096; 0097; 0098; 0099, (2017/01/26)
The invention relates to a method for synthesizing a phosphorus-oxychloride-promoted amide compound. The synthesizing method includes the steps that carboxylic acid serves as one reactant, another reactant (N,N-dialkyl methanamide) serves as a solvent, one equivalent of phosphorus oxychloride is added, and the amide compound is prepared. The reaction substrates are low in price and easy to get, the nature is stable, toxicity is small, the reaction speed is high, conditions are moderate, and the reaction substrates can be widely applied to substrates with different functional groups. The efficiently-constructed amide compound is an important molecular skeleton for many medicines, bioactive molecules and natural products, and the synthesizing method is a widely-applicable preparing method for synthesizing the compound.