25364-68-5Relevant academic research and scientific papers
Magnesium Halide-Catalyzed Synthesis of Oxaspiro[2.5]octenes from a Methylenecyclopropane and Acyl Cyanoalkenes
Ogura, Kazuki,Shibata, Ikuya,Shimazu, Jun-ya,Suzuki, Itaru
supporting information, p. 2785 - 2787 (2021/06/26)
MgX2-catalyzed annulation of methylenecyclopropanes with acyl cyanoalkenes was accomplished to give oxaspiro[2.5]octenes in excellent yields. The reaction proceeded through a rare intramolecular oxa-Michael addition of Mg enolate. The oxaspiro
Substituent-Controlled Divergent Cascade Cycloaddition Reactions of Chalcones and Arylalkynols: Access to Spiroketals and Oxa-Bridged Fused Heterocycles
Chang, Weixing,Kong, Jingyang,Li, Jing,Liu, Lingyan,Wang, Hongkai,Zeng, Tianlong
supporting information, p. 4024 - 4032 (2021/07/12)
Herein, we report substituent-controlled divergent cascade cycloaddition reactions of chalcones and arylalkynols in the presence of PtI2. Depending on the substituent on the chalcone, either spiroketals or oxa-bridged fused heterocycles could be obtained in the ranges of 86–97% and 87–95% yields under identical reaction conditions. Control experiments were carried out to elucidate the origin of the high chemoselectivity. These provide a method for the synthesis of a diverse array of structurally complex oxygen-containing heterocycles. (Figure presented.).
Dienamine-Mediated Asymmetric Inverse-Electron-Demand Hetero-Diels–Alder Reaction of Linear Deconjugated Enones: Diversity-Oriented Synthesis of 3,4-Dihydropyrans
Maity, Rajendra,Pan, Subhas Chandra
supporting information, p. 871 - 874 (2017/02/15)
The first organocatalytic asymmetric inverse-electron-demand Diels–Alder reaction of deconjugated enones by using a linear dienamine was explored. Electron-poor oxadienes having a cyano group were found to be suitable in this reaction. With a 20 mol-% loa
Organocatalytic Asymmetric [4+2] Cycloaddition of 1-Acetylcyclopentene and 1-Acetylcyclohexene for the Synthesis of Fused Carbocycles
Nath, Utpal,Pan, Subhas Chandra
supporting information, p. 6457 - 6461 (2017/12/01)
The first organocatalytic asymmetric [4+2]-cycloaddition reaction of 1-acetylcyclopentenes and 1-acetylcyclohexenes was developed. Enones having cyano groups were used as the dienophiles in this method. The reaction provides a useful practical route to th
Stereospecific synthesis of polysubstituted E-olefins by reaction of acyclic nitrones with free and platinum(II) coordinated organonitriles
Lasri, Jamal,Januario Charmier, M. Adilia,Haukka, Matti,Pombeiro, Armando J. L.
, p. 750 - 755 (2007/10/03)
(Chemical Equation Presented) Free nitriles NCCH2R (1a R = CO2Me, 1b R = SO2Ph, and 1c R = COPh) with an acidic α-methylene react with acyclic nitrones -O+N(Me)= C(H)R′ (2a R′ = 4-MeC6Hsub
Palladium-Catalyzed Acylcyanation of Terminal Arylacetylenes. Synthesis of 1,3-Diaryl-3-cyano-2-propen-1-ones and Tetrasubstituted Furans
Nozaki, Kyoko,Sato, Naomasa,Takaya, Hidemasa
, p. 1629 - 1637 (2007/10/03)
(Z)-1,3-Diaryl-3-cyano-2-propen-1-ones ((Z)-1) are prepared from arenecarbonyl cyanide and terminal arylacetylene in the presence of Pd(OAc)2-PPh3 (1 mol amt. to Pd)-0.5dppb (1,4-bis(diphenylphosphino)butane) (0.5 mol amt. to Pd). The reaction proceeded via the formation of acetylenic ketone 3, followed by the palladium-catalyzed addition of HCN, and isomerization of the resulting (E)-1 to (Z)-1. Oxidative addition of arenecarbonyl cyanide to zero-valent palladium metal has been observed by admixture of 4-MeOC6H4COCN to Pd2(dba)3 · CHCl3-PPh3-0.5dppb oxide (dppb oxide = Ph2P(O)(CH2)4P(O)Ph2). The resulting Pd(4-MeOC6H4CO)(CN)(PPh3)(ligand) afforded (Z)-1c by reaction with phenylacetylene. Thus, the role of two kinds of phosphine, PPh3 and dppb, suggests that the former acts as a ligand and the latter works as a reductant of Pd(II). The product (Z)-1 can be photoisomerized to (E)-1 under room light in CDCl3. The product (Z)-1 was obtained by a four-component coupling reaction of 4-iodotoluene, phenylacetylene, KCN, and carbon monoxide. A new synthesis of tetrasubstituted furans is also mentioned.
