27845-51-8Relevant articles and documents
Reactivity of 3-Oxo-β-lactams with Respect to Primary Amines—An Experimental and Computational Approach
Piens, Nicola,Goossens, Hannelore,Hertsen, Dietmar,Deketelaere, Sari,Crul, Lieselotte,Demeurisse, Lotte,De Moor, Jelle,Van den Broeck, Elias,Mollet, Karen,Van Hecke, Kristof,Van Speybroeck, Veronique,D'hooghe, Matthias
, p. 18002 - 18009 (2017/12/13)
The reactivity of 3-oxo-β-lactams with respect to primary amines was investigated in depth. Depending on the specific azetidin-2-one C4 substituent, this reaction was shown to selectively produce 3-imino-β-lactams (through dehydration), α-aminoamides (thr
Combination of Enabling Technologies to Improve and Describe the Stereoselectivity of Wolff-Staudinger Cascade Reaction
Musio,Mariani,?liwiński,Kabeshov,Odajima,Ley
supporting information, p. 3515 - 3526 (2016/10/18)
A new, single-mode bench-top resonator was evaluated for the microwave-assisted flow generation of primary ketenes by thermal decomposition of α-diazoketones at high temperature. A number of amides and β-lactams were obtained by ketene generation in situ and reaction with amines and imines, respectively, in good to excellent yields. The preferential formation of trans-configured β-lactams was observed during the [2+2] Staudinger cycloaddition of a range of ketenes with different imines under controlled reaction conditions. Some insights into the mechanism of this reaction at high temperature are reported, and a new web-based molecular viewer, which takes advantage from Augmented Reality (AR) technology, is also described for a faster interpretation of computed data.
An effective method to prepare imines from aldehyde, bromide/epoxide, and aqueous ammonia
Huang, Jing-Mei,Zhang, Jue-Fei,Dong, Yi,Gong, Wen
, p. 3511 - 3514 (2011/06/22)
A three-component reaction of aldehydes, alkyl bromides, and ammonia to form imines was studied. Aqueous ammonia was applied as the nitrogen source and solvent in the reaction. For the aromatic aldehyde, the product yields are good to excellent and the reaction conditions are mild to be compatible with a range of functional groups. The reaction of aldehydes and aqueous ammonia with epoxides was also studied and imines bearing a vicinal hydroxyl group can be obtained efficiently and regioselectively. And studies showed that this method allows the synthesis of primary amines and especially 1,2-amino alcohol selectively in high yield. It is proposed that the reaction pathway might involve a key intermediate of hydrobenzamide.