35614-54-1Relevant academic research and scientific papers
Discovery of two new classes of potent monoamine oxidase-B inhibitors by tricky chemistry
Cagide,Silva,Reis,Gaspar,Borges,Gomes,Low
, p. 2832 - 2835 (2015/02/19)
The discovery of potent and selective monoamine oxidase-B inhibitors for the management of neurodegenerative diseases such as Alzheimer's and Parkinson's diseases is still a challenging endeavor. Herein, we report the discovery of two new classes of poten
Water-promoted synthesis of enaminones: Mechanism investigation and application in multicomponent reactions
Liu, Yunyun,Zhou, Rihui,Wan, Jie-Ping
, p. 2475 - 2483 (2013/07/25)
Highly stereoselective synthesis of Z-enaminones bearing reactive secondary amino group has been successfully performed in water using tertiary amino group functionalized enaminones under ambient conditions. An interesting promotion effect of water on the
Deuterium isotope effects on 13C chemical shifts of enaminones
Zheglova, Donka Kh.,Genov, Daniel G.,Bolvig, Simon,Hansen, Poul Erik
, p. 1016 - 1023 (2007/10/03)
Deuterium isotope effects on 13C chemical shifts have been studied in a series of substituted N-alkyl and N-phenyl keto-enamines. The intramolecularly hydrogen bonded Z-forms show the largest two-bond isotope effects, 2δC-1 (ND). Methyl-substitution at C-1 leads to a larger two-bond isotope effect in the N-phenyl-substituted derivatives. This effect is ascribed to steric compression. Space-filling substituents at the ortho-position of the N-phenyl ring lead to a decrease of the two-bond isotope effect. A correlation is found between 2δC-1(ND) and 3δC-2′(ND). The latter becomes negative in the sterically hindered cases. 3δC-2′(ND) may therefore be used as a gauge of the twist of the phenyl ring. o-Hydroxy substitution of the CO-phenyl rings enables intramolecular hydrogen bonding to the carbonyl group. This kind of hydrogen bond with two donors to one acceptor leads to smaller 2δC-2(ND) and 2δC-2″(OD) isotope effects equivalent to weaker hydrogen bonds for the Z-isomer. This is ascribed to competition for the acceptor. For the E-isomer 2δC(OD) is enhanced. The same feature is seen for N,N-dimethylamino enamines. This increase is ascribed to delocalization of the nitrogen lone-pair onto the carbonyl oxygen, thereby strengthening the hydrogen bond and thus leading to larger two-bond, 2δC(OD), isotope effects. Acta Chemica Scandinavica 1997.
