5350-67-4Relevant articles and documents
α-Aminonitrile hydration in the presence of hydrogen peroxide in aqueous basic medium
Taillades, Jacques
, p. 89 - 100 (2007/10/03)
α-Aminonitriles are hydrated into α-aminoamides in the presence of hydrogen peroxide in sodic or ammoniacal basic medium. While the hydration mechanism is close to the mechanism described previously in the case of aromatic nitrites, we showed that, in weakly basic conditions, the amine function of α-aminonitrile is competitively oxidized via a peroxyimidic acid by an intramolecular process. In the case of 2-aminopropanenitrile, this reaction leads to pyruvamide oxime. Furthermore, the study of structurereactivity relationships in the hydration of aliphatic and aromatic monofunctional nitriles and α-aminonitriles showed that the reactivity of the substrates towards hydroperoxide onion, which mostly depends on inductive effects of the substituents, is sufficiently enhanced to allow hydration of tertiary α-aminonitriles with low steric hindrance and regioselective hydration of dissymmetric α-aminodinitriles. Eisevier,.
C-C - CONNECTIVE SYNTHESIS OF α-DIALKYLAMINO - KETONES FROM ALDEHYDES AND SEC.-AMINES
Enders, Dieter,Lotter, Hermann
, p. 639 - 642 (2007/10/02)
A simple and efficient 3 - step synthesis of α-dialkylamino - ketones 3 starting from aldehydes and sec.-amines is described.The unsymmetrically aminoketones are obtained as pure regioisomers via reaction of metalated α-aminonitriles 1 with aldehydes, followed by thermal HCN-elimination/tautomerization.