1373253-95-2Relevant academic research and scientific papers
Copper-Catalyzed N -Arylation of Azoles and Mannich-Type Coupling of Ketones and Azoles under Metal-Free Conditions
Sun, Kai,Zhu, Zhonghong,Sun, Jingjing,Liu, Lulu,Wang, Xin
, p. 1476 - 1483 (2016/03/01)
(Chemical Equation Presented) A new process has been developed for the copper-catalyzed direct N-arylation of five-membered heterocycles with azoles. Five-membered heterocycles bearing an acetyl group also underwent a Mannich-type reaction with activated azoles to give the corresponding β-amino ketones under metal-free conditions. These reactions exhibited wide substrate scope, high functional group tolerance, and ease of operation, making them useful tools with numerous potential applications in synthetic chemistry.
A convenient approach to β-heteroarylated (C-N bond) ketones from Cs2CO3 promoted reaction between propargyl alcohols and nitrogen-heterocycles
Bhanuchandra,Kuram, Malleswara Rao,Sahoo, Akhila K.
, p. 3538 - 3555 (2012/05/20)
An efficient and direct approach to β-heteroarylated (C-N bond) ketones is demonstrated. Base promoted redox isomerization of propargyl alcohol to α,β-unsaturated ketone followed by conjugate addition to NH-heteroarenes affords a wide range of β-heteroarylated ketones in good to excellent yields. Aryl, heteroaryl, alkyl C(sp), and terminal alkynes containing unactivated propargyl alcohols effectively undergo redox-isomerization conjugate addition (RICA) with NH-heteroarenes. Reaction of 3-substituted pyrazoles or indazole with propargyl alcohols enables highly regioselective products. A diverse range of NH-bearing nucleophiles such as: pyrazoles, imidazole, triazoles, pyrrole, indoles and aniline participate in this reaction and deliver the corresponding β-heteroarylated ketones.
