18033-63-1Relevant academic research and scientific papers
Regiocomplementary cycloaddition reactions of boryl- and silylbenzynes with 1,3-dipoles: Selective synthesis of benzo-fused azole derivatives
Ikawa, Takashi,Takagi, Akira,Goto, Masahiko,Aoyama, Yuya,Ishikawa, Yoshinobu,Itoh, Yuji,Fujii, Satoshi,Tokiwa, Hiroaki,Akai, Shuji
, p. 2965 - 2983 (2013/06/26)
Benzo-fused nitrogen-containing heterocycles are abundant in biologically active compounds. One of the most important methods for preparing such heterocycles is the (3 + 2) cycloaddition reaction of benzynes with 1,3-dipolar compounds. However, the reacti
Ortho-selective nucleophilic addition of primary amines to silylbenzynes: Synthesis of 2-silylanilines
Ikawa, Takashi,Nishiyama, Tsuyoshi,Shigeta, Takashi,Mohri, Shinya,Morita, Shinsuke,Takayanagi, Sho-Ichi,Terauchi, Yuki,Morikawa, Yuki,Takagi, Akira,Ishikawa, Yoshinobu,Fujii, Satoshi,Kita, Yasuyuki,Akai, Shuji
supporting information; experimental part, p. 5674 - 5677 (2011/08/06)
Cause and effect: The first ortho-selective nucleophilic addition reaction of amines to 3-substituted benzynes has been achieved. Despite a large trimethylsilyl substituent, primary amines attack the C2 position of 3-silylbenzynes to produce 2-silylanilines (see scheme). This outcome is likely to result from the inductive electron-donating effect of the silyl group, which overrides its steric repulsion with the approaching amines. Copyright
Regioselective and stereoselective cyclizations of cyclohexadienones tethered to active methylene groups
Tello-Aburto, Rodolfo,Kalstabakken, Kyle A.,Volp, Kelly A.,Harned, Andrew M.
supporting information; experimental part, p. 7849 - 7859 (2011/12/04)
The cyclization of 2,5-cyclohexadienones tethered to activated methylene groups was studied. The substitution around the cyclohexadienone ring serves to regioselectively direct these cyclizations based primarily on electronic effects. In the case of brominated substrates, these reactions proceed to give highly unusual electron-deficient tricyclic cyclopropanes. By using a Cinchona alkaloid-based phase-transfer catalyst, prochiral cyclohexadienones can be desymmetrized with moderate stereoselectivity.
