122709-95-9Relevant academic research and scientific papers
Graphene Oxide: A Metal-Free Carbocatalyst for the Synthesis of Diverse Amides under Solvent-Free Conditions
Patel, Khushbu P.,Gayakwad, Eknath M.,Patil, Vilas V.,Shankarling, Ganapati S.
, p. 2107 - 2116 (2019)
An environmentally friendly, inexpensive, carbocatalyst, graphene oxide (GO) promoted efficient, metal-free transamidation of various carboxamides with aliphatic, cyclic, and aromatic amines is demonstrated. The protocol is equally applicable to phthalimide, urea, and thioamide determining its adaptability. The oxygenated functionalities such as carbonyl (?C=O), epoxy (?O?), carboxyl (?COOH) and hydroxyl (?OH), present on graphene oxide surface impart acidic properties to the catalyst. The graphene oxide being heterogeneous in nature, work efficiently under solvent-free reaction conditions providing desired products in good to excellent yields. The one-pot synthesis of 2,3-Dihydro-5H-benzo[b]-1,4-thiazepin-4-one moiety by GO catalyzed Aza Michael addition followed by intramolecular transamidation is also described. A plausible reaction mechanistic pathway involving H-bonding is discussed. The graphene oxide can be recycled and reused up to five cycles without much loss in catalytic activity. (Figure presented.).
X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES. PART 20. DECARBOXYLATION OF α-IMINO ACIDS. MECHANIZM AND APPLICATIONS TO THIOAMIDE SYNTHESIS
Aly, Moustafa F.,Grigg, Ronald
, p. 7271 - 7282 (2007/10/02)
α-Imino acids, prepared from α-keto acids and primary amines, undergo facile decarboxylation to the corresponding imines on heating at =80 deg C in benzene or methylene chloride.Decarboxylation proceeds via a 1,2-ylide which can be trapped by sulphur to give the corresponding secondary thioamides in good yield. 1,2-Ylides from secondary amines and α-keto acids can be generated in situ and trapped with sulphur to give tertiary thioamides in excellent yield.
Ready Decarboxylation of Imines of α-Keto Acids. Mechanism and Application to Thioamide Synthesis
Aly, Moustafa F.,Grigg, Ronald
, p. 1523 - 1524 (2007/10/02)
α-Keto acids are readily decarboxylated via imine formation with primary and/or secondary amines even when imine-enamine isomerisation can occur; the process is thought to involve an intermediate zwitterion which can be trapped by sulphur to give thioamides in excellent yield.
