79892-21-0Relevant articles and documents
One-Pot Synthesis of 2-Cyano-1,4-diketones: Applications to Synthesis of Cyanosubstituted Furans, Pyrroles, and Dihydropyridazines
Chan, Chieh-Kai,Chan, Yi-Ling,Tsai, Yu-Lin,Chang, Meng-Yang
, p. 8112 - 8120 (2016/09/12)
A convenient synthetic route for the construction of functionalized 2-cyano-1,4-diketones has been established from the nucleophilic substitution of 2-bromoacetophenones with NaCN via the in situ-generated β-ketonitriles. This method was further applied to the synthesis of cyanosubstituted furans, pyrroles, or dihydropyridazines, which were obtained in good to excellent yields using Bi(OTf)3, NH4OAc, or N2H4. The key structures were confirmed by X-ray single crystal diffraction analysis.
N-heterocyclic carbene-catalyzed annulation of α-cyano-1,4-diketones with ynals
Romanov-Michailidis, Fedor,Besnard, Celine,Alexakis, Alexandre
supporting information, p. 4906 - 4909,4 (2012/12/12)
In this paper, the first stereoselective annulation reaction between r-cyano-1,4-diketones and ynals, mediated by catalytic amounts of a triazolium salt precatalyst and cocatalytic amounts of a weak carboxylate base, is disclosed. The title transformation proceeds smoothly under mild reaction conditions and generates three contiguous stereogenic centers, one of which is a quaternary acetal carbon. This reaction tolerates a wide variety of electronically distinct substituents on both reaction partners and affords privileged bicyclic scaffolds in 61-90% isolated yields and with up to 20:1 diastereomeric preference.
N-heterocyclic carbene-catalyzed annulation of α-cyano-1,4-diketones with ynals
Romanov-Michailidis, Fedor,Besnard, Céline,Alexakis, Alexandre
supporting information, p. 4906 - 4909 (2013/01/15)
In this paper, the first stereoselective annulation reaction between r-cyano-1,4-diketones and ynals, mediated by catalytic amounts of a triazolium salt precatalyst and cocatalytic amounts of a weak carboxylate base, is disclosed. The title transformation proceeds smoothly under mild reaction conditions and generates three contiguous stereogenic centers, one of which is a quaternary acetal carbon. This reaction tolerates a wide variety of electronically distinct substituents on both reaction partners and affords privileged bicyclic scaffolds in 61-90% isolated yields and with up to 20:1 diastereomeric preference.
EtOH/Ba(OH)2 triggers self-condensation of (E)-1,4-diaryl-2- butene-1,4-diones to cyclopentanol derivatives
Rao, H. Surya Prakash,Senthilkumar
, p. 1707 - 1714 (2007/10/03)
Several stereo-defined penta-substituted cyclopentanols were synthesized from EtOH/Ba(OH)2-induced self-condensation of (E)-1,4-diaryl-2- butene-1,4-diones formed via domino pathways. Copyright Taylor & Francis, Inc.
Olefin-insertion reaction between the carbonyls of benzils; formation of 1,4-diketones by Michael Additon catalyzed by Cyanide Ion
Miyashita, Akira,Numata, Atsushi,Suzuki, Yumiko,Iwamoto, Ken-Ichi,Higashino, Takeo
, p. 697 - 698 (2007/10/03)
Benzils (1) react with Michael addition acceptors (2) in the presence of cyanide ion as a catalyst to give 1,4-diketones (3), which are products of ethy lene group insertion between the carhonyls of the benzils. The 1,4-diketones (3) are produced through
Manganese(III)-based facile synthesis of 3-cyano-4,5-dihydrofurans and 4-cyano-1,2-dioxan-3-ols using alkenes and acylacetonitrile building blocks
Nguyen, Van-Ha,Nishino, Hiroshi,Kurosawa, Kazu
, p. 899 - 908 (2007/10/03)
New 3-cyano-4,5-dihydrofurans and 4-cyano-1,2-dioxan-3-ols were alternatively synthesized in good yields by the oxidation of acylacetonitrile building blocks with manganese(III) acetate in the presence of alkenes without any byproducts. The reaction at reflux temperature gave 3-cyano-4,5-dihydrofurans under an argon atmosphere, while 4-cyano-1,2-dioxan-3-ols were obtained at 23°C under an air atmosphere except for the reaction of styrene with benzoylacetonitrile which afforded 2-cyano-1,4-diphenylbutane-1,4-dione, and the reaction of 1,1-diphenylethene with 2-(2-cyano-1-oxoethyl)-5-methylfuran which yielded 2-cyano-4,4-diphenylbutanolide without any cyclic peroxides. The oxidation of benzoylacetonitrile itself at 23°C under an air atmosphere in the absence of alkene gave benzoic acid. Easy conversion of the 1,2-dioxanes to furans was demonstrated, and mechanisms for the formation of dihydrofurans and dioxanes as well as the unusual transformation to butanedione and butanolide were also discussed.
THE SYNTHESIS AND CHEMISTRY OF AZOLENINES. PART 17. THE PREPARATION AND THE CRYSTAL AND MOLECULAR STRUCTURE OF 3-METHYL-2,5-DIPHENYL-3H-PYRROLE-3-CARBONITRILE
Chiu, Pak-Kan,Lai, Ting-Pong,Sammes, Michael P.
, p. 428 - 439 (2007/10/02)
The structure of the title compound has been determined.Bond parameters are compared with those for two previously reported structures of 3H-pyrroles, and with literature data from molecular orbital calculations for the parent (ab initio) and for 3,3,4-trimethyl-2,5-diphenyl-3H-pyrrole (MINDO/3).
Hunig's Base-Magnesium Chloride Mediated Carbon Alkylation and Oxygen Acylation of Benzoylacetonitrile
Mansour, Tarek S.
, p. 3437 - 3440 (2007/10/02)
In the presence of Hunig's base and anhydrous magnesium chloride, benzoylacetonitrile (1) reacts with 2-haloketones and -esters to give C-alkylated products which may cyclize to polysubstituted furans whereas with acid chlorides O-acylated products are obtained as separable mixtures of E and Z isomers.
