115-80-0Relevant articles and documents
Structural determination, DFT Calculation, and Formation Mechanism of Ethyl 2-Cyano-3-Alkoxypent-2-enoates synthesized via Ru-mediated coupling reaction between α,β-unsaturated acetals and cyanoacetate
Seino, Hidetake,Kondo, Takumi,Mochizuki, Chihiro,Tokunaga, Ken,Yamaguchi, Motowo,Sato, Mitsunobu
, p. 79 - 87 (2017)
Ethyl 2-cyano-3-Alkoxypent-2-enoates were synthesized in moderate yields via the coupling reaction between α,β- unsaturated acetals and cyanoacetate, catalyzed by [RuHCl- (CO)(PPh3)3]. The E-And Z-isomers were separated and determined by X-ray crystallography for the first time. Structural distortion associated with steric hindrance around the tetrasubstituted alkene moiety was revealed: e.g., the C(carbonyl)C( α)C( β) angle expands to about 125°. Density functional theory calculation was performed, and the restricted B3LYP hybrid functional with the 6-31G(d,p) basis set was found to successfully elucidate the solid-state structure and conformation, as well as spectroscopic properties. A plausible formation mechanism was proposed, in which the Ru complex catalyzed the C=C bond migration of the α,β-unsaturated acetal to give the corresponding ketene acetal and assisted the subsequent condensation reaction with cyanoacetate to some extent.
AN EXPEDITIOUS ROUTE TO MONOPROTECTED α-KETO ALDEHYDES WITH CONTROL OF REGICHEMISTRY
Babler, James H.
, p. 355 - 358 (2007/10/02)
Treatment of representative orthoesters (2) with pyruvonitrile (3) afforded the corresponding α,α-diethoxynitriles (4) in 65-85percent yields.Subsequent reduction of the latter using lithium aluminium hydride, followed by careful hydrolysis of the aldimine intermediates, led to the procurement of α,α-doalkoxy aldehydes (5) in 80-90percent yield.
Method of using [1,2,4]triazolo[4,3-a]quinoxaline-4-amine derivatives as antidepressant and antifatigue agents
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, (2008/06/13)
A series of novel [1,2,4]triazolo[4,3-a]quinoxaline-4-amine derivatives wherein the amine group is optionally substituted with lower alkyl, phenylalkyl having up to three carbon atoms in the alkyl moiety or alkanoyl having from two to five carbon atoms, or the amine group alternatively completes a piperazino ring, the quinoxaline ring is optionally substituted with fluorine, chlorine, bromine or methoxy, and the triazolo ring is optionally substituted with lower alkyl, lower perfluoroalkyl or phenyl are disclosed. These novel compounds are useful for treatment of symptoms associated with depression. Also disclosed are pharmaceutical compositions containing the novel compounds of this invention and a method of using the compounds in the treatment of depression and fatigue.
Method of using [1,2,4]triazolo[4,3-a]quinoxaline-4-amine derivatives as antidepressant and antifatigue agents
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, (2008/06/13)
A series of novel [1,2,4]triazolo[4,3-a]quinoxaline-4-amine derivatives wherein the amine group is optionally substituted with lower alkyl, phenylalkyl having up to three carbon atoms in the alkyl moiety or alkanoyl having from two to five carbon atoms, or the amine group alternatively completes a piperazino ring, the quinoxaline ring is optionally substituted with fluorine, chlorine, bromine or methoxy, and the triazolo ring is optionally substituted with lower alkyl, lower perfluoroalkyl or phenyl are disclosed. These novel compounds are useful for treatment of symptoms associated with depression. Also disclosed are pharmaceutical compositions containing the novel compounds of this invention and a method of using the compounds in the treatment of depression and fatigue.
Process for preparation of adjacently disubstituted ketones
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, (2008/06/13)
A novel 7-hydroxyprostaglandin E1, or a stereoisomer thereof, or a protected derivative thereof, having the following formula: STR1 wherein R8 represents H, CH3 or C2 H5, R9 represents H or CH3, R10 and R11 are identical or different, and each represents H, tetrahydropyranyl or t-butyldimethylsilyl. Also provided is a process for producing an adjacently disubstituted ketone including the above compounds, i.e. 7-oxoprostaglandin, etc. which comprises reacting an α,β-unsaturated carbonyl compound with a cuprous salt and an organolithium compound in an aprotic inert organic medium in the presence of trialkylphosphine, the amounts of said cuprous salt and said organolithium compound being substantially equimolar, and reacting the product with a protected acetal derivative of an organic carbonyl compound or an aldehyde in the presence of a Lewis acid, if necessary, followed by reacting the product with a proton donor.
