141809-66-7Relevant articles and documents
A versatile, practical, and inexpensive reagent, pyridine-3-carboxylic anhydride (3-PCA), for condensation reactions
Funasaka, Setsuo,Mukaiyama, Teruaki
, p. 148 - 159 (2008)
A highly useful method for the preparation of carboxylic esters and carboxamides from various carboxylic acids was established by using a novel condensing reagent, pyridine-3-carboxylic anhydride (3-PCA), in the presence of 4-(dimethylamino)pyridine as an activator. The reactions of various carboxylic acids with nucleophiles, such as alcohols or amines, afforded the corresponding carboxylic acids or carboxamides in good to high yields under mild conditions by using simple experimental procedure. In addition, it was confirmed that this protocol was applicable to a gram-scale synthesis and the by-products, including pyridine-3-carboxylic acid and pyridine-3-carboxylate (or pyridine-3- carboxamide) produced in situ, were easily removed by using a simple aqueous workup.
The Esterification Reaction between Silyl Derivatives of Carboxylic Acids and Alcohols by the Promotion of a Catalytic Amount of Lewis Acid
Shiina, Isamu,Mukaiyama, Teruaki
, p. 2319 - 2320 (1992)
Various carboxylic esters are prepared in good to excellent yields by the reaction of equimolar amounts of silyl derivatives of carboxylic acid and alcohols by using a catalytic amount of active Lewis acid in hexamethyldisiloxane, a solvent.
Amines vs. N-Oxides as Organocatalysts for Acylation, Sulfonylation and Silylation of Alcohols: 1-Methylimidazole N-Oxide as an Efficient Catalyst for Silylation of Tertiary Alcohols
Murray, James I.,Spivey, Alan C.
, p. 3825 - 3830 (2016/01/25)
A comparison of the relative catalytic efficiencies of Lewis-basic amines vs. N-oxides for the acylation, sulfonylation and silylation of primary, secondary and tertiary alcohols is reported. Whilst the amines are generally superior to the N-oxides for acylation, the N-oxides are superior for sulfonylation and silylation. In particular, 1-methylimidazole N-oxide (NMI-O) is found to be a highly efficient catalyst for sulfonylation and silylation reactions. To the best of our knowledge, NMI-O is the first amine or N-oxide Lewis basic organocatalyst capable of promoting the efficient silylation of tert-alcohols in high yield with low catalyst loading under mild reaction conditions.
A new method for the synthesis of carboxylic esters and lactones with di-2-thienyl carbonate (2-DTC) by the promotion of DMAP and iodine
Oohashi, Yoshiaki,Fukumoto, Kentarou,Mukaiyama, Teruaki
, p. 1508 - 1519 (2007/10/03)
The esterification of carboxylic acids with alcohols by using di-2-thienyl carbonate (2-DTC) in the presence of a catalytic amount of 4-(dimethylamino) pyridine (DMAP) proceeded smoothly to afford the corresponding esters in good-to-high yields along with 2(5H)-thiophenone. This esterification was accelerated by the addition of an equimolar amount of iodine to afford the esters in higher yields within a shorter reaction time. Further, cyclization of ω-hydroxycarboxylic acids with an equimolar amount of 2-DTC in the presence of a catalytic amount of DMAP, followed by the addition of 1-4 equimolar amounts of iodine, afforded the corresponding lactones in good-to-high yields under mild conditions. This method was successfully employed in the synthesis of erythro-aleuritic acid lactone.
