5334-06-5Relevant articles and documents
Electroselective and Controlled Reduction of Cyclic Imides to Hydroxylactams and Lactams
Bai, Ya,Shi, Lingling,Zheng, Lianyou,Ning, Shulin,Che, Xin,Zhang, Zhuoqi,Xiang, Jinbao
supporting information, p. 2298 - 2302 (2021/04/05)
An efficient and practical electrochemical method for selective reduction of cyclic imides has been developed using a simple undivided cell with carbon electrodes at room temperature. The reaction provides a useful strategy for the rapid synthesis of hydroxylactams and lactams in a controllable manner, which is tuned by electric current and reaction time, and exhibits broad substrate scope and high functional group tolerance even to reduction-sensitive moieties. Initial mechanistic studies suggest that the approach heavily relies on the utilization of amines (e.g., i-Pr2NH), which are able to generate α-aminoalkyl radicals. This protocol provides an efficient route for the cleavage of C-O bonds under mild conditions with high chemoselectivity.
Reaction of phthalaldehyde with aminoethanol under different conditions: Products and mechanisms of their formation
Klima, Jiri,Polasek, Miroslav,Ludvik, Jiri,Urban, Jiri
, p. 1202 - 1209 (2013/01/15)
Analysis of amino acids and very efficient disinfection procedures are based on the reaction of phthalaldehyde (OPA) with primary amines. In this contribution, aminoethanol (=kolamin) as a nitrogen-containing nucleophile was used for the investigation of its reaction mechanism with OPA performed in basic aqueous buffered media (pH 9.5), where an influence of hydration or solvation is expected, and in anhydrous acetonitrile. Depending on the detailed reaction conditions, seven products were isolated and their structures determined by NMR, mass spectrometry, and X-ray structure analysis. Reaction mechanisms are proposed, which involve hydride transfers to OPA (Cannizzaro-type reaction).
Complementary synthetic approaches to constitutionally diverse N-aminoalkylated isoindolinones: Application to the synthesis of falipamil and 5-HT1A receptor ligand analogues
Lorion, Magali,Couture, Axel,Deniau, Eric,Grandclaudon, Pierre
experimental part, p. 1897 - 1903 (2010/02/16)
Different synthetic approaches for the elaboration of poly and diversely substituted isoindolinones tailed with constitutionally diverse aminoalkylated chains have been developed. The key step is based upon the preliminary assembly of the isoindolinone te
