1398565-76-8Relevant 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, 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.
