46721-86-2Relevant articles and documents
Reductive N-alkylation of amides, carbamates and ureas
Dube, Daniel,Scholte, Andrew A.
, p. 2295 - 2298 (1999)
A one pot selective mono N-alkylation of primary amides, thioamides, carbamates and ureas has been developed using aromatic and aliphatic aldehydes as alkylating agents and trifluoroacetic acid / triethylsilane as reagents. Application to an efficient synthesis of a primary amine from the corresponding aldehyde via the carbamate intermediate is presented.
Reductive Amidation without an External Hydrogen Source Using Rhodium on Carbon Matrix as a Catalyst
Tsygankov, Alexey A.,Makarova, Maria,Afanasyev, Oleg I.,Kashin, Alexey S.,Naumkin, Alexander V.,Loginov, Dmitry A.,Chusov, Denis
, p. 112 - 117 (2019/11/28)
An efficient method for preparation of secondary amides from primary amides and aldehydes using rhodium on carbon matrix as catalyst was developed. The method does not require any external hydrogen source and carbon monoxide is used as a reducing agent. The most active rhodium catalysts were characterized by BET, TEM and XPS techniques. Unexpectedly, it was found that heterogeneous rhodium on carbon matrix works as precatalyst for homogenous active species due to leaching of rhodium to the solution. Various secondary amides were synthesized and checked for antifungal activity. 4-Methoxy-N-(4-methoxybenzyl)benzamide demonstrated promising activity against Rhizoctonia Solani.
Direct Amidation of Carboxylic Acids through an Active α-Acyl Enol Ester Intermediate
Xu, Xianjun,Feng, Huangdi,Huang, Liliang,Liu, Xiaohui
, p. 7962 - 7969 (2018/06/18)
The development of a highly efficient and simple protocol for the direct amidation of carboxylic acids is described employing ynoates as novel coupling reagents. The transformation proceeds in good to excellent yields via in situ α-acyl enol ester intermediates formation under mild reaction conditions. This useful method has been demonstrated for a range of substrates to provide a succinct access to structurally diverse amides, including key intermediates of glibenclamide, tiapride hydrochloride, and nateglinide, and can be conducted on a mole scale.
