Sonogashira coupling reactions: Synthesis of 4-substituted-6-methyl-2-(methylthio)pyrimidines catalyzed by Pd–Cu

2019 ◽  
Vol 43 (9-10) ◽  
pp. 431-436
Author(s):  
Fatemeh Rezaeimanesh ◽  
Mohammad Bakherad ◽  
Hossein Nasr-Isfahani

An efficient method is developed for the synthesis of 4-(3-arylprop-2-ynyloxy)-6-methyl-2-(methylthio)pyrimidines via palladium-catalyzed Sonogashira reactions of 4-methyl-2-(methylthio)-6-(prop-2-yn-1-yloxy)pyrimidine with electron-poor aryl iodides in acetonitrile at room temperature. Excellent yields of the products were obtained in reaction times of 9–11 h.

Synthesis ◽  
2021 ◽  
Author(s):  
George A. Kraus ◽  
Joshua L Alterman

A modified Sonogashira coupling of aryl iodides and propyne was achieved using only two equivalents of propyne in THF from -78°C to room temperature.


Synlett ◽  
2021 ◽  
Author(s):  
Yadong Sun ◽  
Ablimit Abdukader ◽  
Yuhan Lu ◽  
Chenjiang Liu

AbstractA highly efficient method for the synthesis of 1,2,3-thiadiazoles has been developed by utilizing readily available tosylhydrazones and ammonium thiocyanate with ecofriendly EtOH as the solvent at room temperature. The reaction shows a wide scope of substrates and good functional-group tolerance. This protocol can be scaled up to a gram level and can be applied to coupling reactions with 4-(4-bromophenyl)-1,2,3-thiadiazole as the substrate.


2019 ◽  
Vol 53 (2) ◽  
Author(s):  
Shahriar Ghammamy ◽  
Samira Khorsandtabar ◽  
Ali Moghimi ◽  
Hajar Sahebalzamani

A mild and efficient method for the mono-oxidation of diols to the corresponding hydroxyaldehydes with trialkylammonium fluorochromates(VI), R3NH[CrO3F] (R= CH3, C2H5, C3H7 and C4H9), in solution at room temperature, and in solution under microwave radiation, is reported. The easy procedure, simple work-up, short reaction times, and excellent yields are advantages of these reagents.


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