Synthesis Corner

DMSO/I2 Metal-Free Oxidative α-Nitration of Ketones: A Route to One-Pot Synthesis of Thiohydroximic Acids from Acetophenones

Recently, Batra et al. have reported another new DMSO/I2 metal-free route to functionalize ketones at the α-position.1 Their previous work had demonstrated a DMSO/I2/NaNO2-mediated route to the synthesis of highly substituted isoxazoles.2 Building on this work, they have developed a metal-free route using DMSO/I2/NaNO2 to nitrate the alpha position of ketones. Optimization indicated that, while [...]

DMSO as a Methylene Synthon: Synthesis of Bisimidazopyridinylmethanes

Instances of synthetic methods using DMSO as a reagent/synthon have grown in recent years.  Review articles in 2016 highlight the many functional units that may be installed from DMSO   (-O, -SMe, -CH2SMe, -SO2Me, -Me, -CN, -CHO, and –CH2- ).1,2  Among these recent reports are reactions using DMSO to provide a one-carbon methylene linker between imidazo[1,2-a]heterocycles.3-5  [...]

One-Pot Copper(I)-Catalyzed Synthesis of Quinazolinones in DMSO from Aldehydes, Benzyl Alcohols or Methyl Arenes

Work toward the efficient synthesis of quinazolin-4-(3H)-ones has continued to garner much attention.  Quinazolin-4-(3H)-ones are the core structural components in a variety of drugs and drug candidates and are known to convey numerous pharmacological and biological activities.  Routes to quinazolinones with substitution at the 2-position (1 in Equation 1) are especially important.   Interestingly, many of [...]