80385-43-9Relevant academic research and scientific papers
INTRAMOLECULAR RING CLOSURE OF α,β-UNSATURATED 3-ACYLINDOLES
Bergman, Jan,Venemalm, Lennart
, p. 3741 - 3744 (1987)
A number of unsaturated 3-acylindoles were prepared and annulated ( with HCl or NaCl-AlCl3 ) to 3,4-dihydrocyclopentindol-1(2H)-ones or 1,2,3,9-tetrahydro-4H-carbazol-4-ones depending on the structure of the substrate and/or the reaction conditions.
Intramolecular Nitrofuran Diels-Alder Reactions: Extremely Substituent-Tolerant Cycloadditions via Asynchronous Transition States
Cowie, Thomas Y.,Veguillas, Marcos,Rae, Robert L.,Rougé, Mathilde,Zurek, Justyna M.,Prentice, Andrew W.,Paterson, Martin J.,Bebbington, Magnus W. P.
, p. 6656 - 6670 (2017/07/15)
Nitrofurans undergo intramolecular Diels-Alder reactions with tethered electron-poor dienophiles more rapidly and in higher yield than non-nitrated furans. Computational studies indicate that increased stabilization of a partial positive charge on the nitro-substituted carbon in both transition state and product is the driving force for these reactions. Frontier molecular orbital energy differences indicate a switch from normal to inverse electron demand upon nitration. There does not appear to be a contribution from any differences in aromatic stabilization energy between furans and nitrofurans. Calculations show that the nitrofuran reactions proceed via a highly asynchronous transition state allowing easier bond formation between two sterically hindered carbons.
Pd-Catalyzed α-Selective C-H Functionalization of Olefins: En Route to 4-Imino-β-Lactams
Kong, Wei-Jun,Liu, Yue-Jin,Xu, Hui,Chen, Yan-Qiao,Dai, Hui-Xiong,Yu, Jin-Quan
supporting information, p. 2146 - 2149 (2016/03/05)
Pd-catalyzed α-olefinic C-H activation of simple α,β-unsaturated olefins has been developed. 4-imino-β-lactam derivatives were readily synthesized via activation of α-olefinic C-H bonds with excellent cis stereoselectivity. A wide range of heterocycles at the β-position are compatible with this reaction. The product of 4-imino-β-lactam derivatives can be readily converted to 2-aminoquinoline which exists extensively in pharmaceutical drugs and natural products.
Diastereoselective synthesis of the model insect antifeedants related to azadiradione and epoxyazadiradione based on intramolecular insertion of α- aryl-α-diazoketones
Fernandez-Mateos,Pascual Coca,Perez Alonso,Rubio Gonzalez,Simmonds,Blaney
, p. 14989 - 14998 (2007/10/03)
A new practical and stereoselective method for the synthesis of the model insect antifeedant CDE fragment of azadiradione and epoxyazadiradione, based on intramolecular insertion of α-aryl-α-diazoketones, has been developed. The procedure can be applied to complex systems. A short SAR study is reported.
Thermal Conversion of Phorone into Isophorone via (Trimethylsilyl)oxyhexatriene (SOH) Cyclization
Torok, Daniel S.,Scott, William J.
, p. 3067 - 3070 (2007/10/02)
Heating of 3-Z-4-(trimethylsilyl)oxy-2,6-dimethylhepta-1,3,5-triene, readily available from phorone (LDA; TMSCl), at 220 deg C caused isomerization and cyclization to afford isophorone after deprotection.
