One-Pot Synthesis of γ-Azidobutyronitriles and Their Intramolecular Cycloadditions
Efficient gram-scale, one-pot approaches to azidocyanobutyrates and their amidated or decarboxylated derivatives have been developed, starting from commercially available aldehydes and cyanoacetates. These techniques combine (1) Knoevenagel condensation,
Ivanov, Konstantin L.,Tukhtaev, Hamidulla B.,Tukhtaeva, Feruza O.,Bezzubov, Stanislav I.,Melnikov, Mikhail Ya.,Budynina, Ekaterina M.
p. 3356 - 3373
(2020/09/15)
One-pot esterification and amide formation via acid-catalyzed dehydration and ritter reactions
Esterification of carboxylic acid is achieved using acetonitrile as a water trap. Water liberated during esterification is consumed in cyanide hydrolysis, thereby driving the esterification to completion. Substrates having carboxylic acid and nitrile groups undergo intramolecular dehydration and rehydration to amido esters in the absence of acetonitrile. Cyano acids also undergo esterification and Ritter reaction in one pot when excess alcohol is used. For the first time, we have observed an interesting Ritter reaction of primary alcohols, leading to ester amide product in one pot. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]
Dawar, Pankaj,Raju, M. Bagavan,Ramakrishna, Ramesha Andagar
supporting information
p. 836 - 846
(2014/03/21)
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