4344-71-2Relevant academic research and scientific papers
One-Pot Amide Bond Formation from Aldehydes and Amines via a Photoorganocatalytic Activation of Aldehydes
Papadopoulos, Giorgos N.,Kokotos, Christoforos G.
, p. 7023 - 7028 (2016/08/30)
A mild, one-pot, and environmentally friendly synthesis of amides from aldehydes and amines is described. Initially, a photoorganocatalytic reaction of aldehydes with di-isopropyl azodicarboxylate leads to an intermediate carbonyl imide, which can react with a variety of amines to afford the desired amides. The initial visible light-mediated activation of a variety of monosubstituted or disubstituted aldehydes is usually fast, occurring in a few hours. Following the photocatalytic reaction, addition of the primary amine at room temperature or the secondary amine at elevated temperatures leads to the corresponding amide from moderate to excellent yields without epimerization. This methodology was applied in the synthesis of Moclobemide, a drug against depression and social anxiety.
Amidation through carbamates
Latorre, Antonio,Rodríguez, Santiago,Izquierdo, Javier,González, Florenci V.
experimental part, p. 2653 - 2655 (2009/08/09)
N-Alkyl carbamates of primary amines are easily converted into amides under treatment with Grignard reagents. Consequently, primary amines can be converted into amides in a one-pot reaction through carbamate protection and Grignard addition.
The extraordinary reactions of phenyldimethylsilyllithium with N,N-disubstituted amides
Buswell, Marina,Fleming, Ian,Ghosh, Usha,Mack, Stephen,Russell, Matthew,Clark, Barry P.
, p. 3006 - 3017 (2007/10/03)
The reactions of the silyllithium reagent with tertiary amides was discussed. The enediamines were easily isomerized from cis to trans, easily oxidized to dienediamines and were hydrolyzed to α-aminoketones. If the two equivalents of the silyllithium reagent were used, the product was an α-silylamine. The results show that each member of the homologous series of amides gives rise to a substantially different product.
Preparation and 3-Aza-Cope Rearrangement of N-Alkyl-N-allyl Enamines
Cook, Gregory R.,Stille, John R.
, p. 5578 - 5583 (2007/10/02)
The charge-accelerated rearrangement of N-allyl-N-isobutyl enamine substrates to γ,δ-unsaturated imine products and subsequent reduction to the corresponding N-alkyl δ,ε-unsaturated amines is reported.Several routes to the N-allyl-N-isobutyl enamine
Cp2TiCl2-CATALYZED REACTION OF GRIGNARD REAGENTS WITH ISOCYANATES, FORMATION OF CARBOXAMIDE WITH REARRANGED CARBONSKELETON
Zhang, Yongmin,Jiang, Jinlong,Chen, Yongqian
, p. 3815 - 3816 (2007/10/02)
Isocyanates react with isopropyl or sec-butylmagnesium bromide in the presence of a small amount of Cp2TiCl2 to afford amides with normal alkyl group.A possibl mechanism for this reaction is proposed.
