Use of a readily removable auxiliary group for the synthesis of pyrrolidones by the palladium-catalyzed intramolecular amination of unactivated γ C(sp3)-H Bonds
Easy on, easy off: Directing groups found to promote the palladium-catalyzed amination of γ C(sp3)-H and C(sp 2)-H bonds of secondary amides included 5-methoxy-8-aminoquinoline, which can be removed under mild conditions (see scheme; CAN=ceric ammonium nitrate). In conjunction with a β-C-H methylation or γ-C-H arylation step, the γ-C(sp3)-H amination provided access to complex pyrrolidones from readily available precursors. Copyright
He, Gang,Zhang, Shu-Yu,Nack, William A.,Li, Qiong,Chen, Gong
supporting information
p. 11124 - 11128
(2013/10/22)
Synthesis of 5-hydroxyquinolines
A series of 5-hydroxyquinolines has been prepared via the Skraup reaction. Several regioisomers were made either by selective displacement of a leaving group or by using a bromo substituent as a blocking group. The bromo group was found to be an excellent blocking group due to its stability during the Skraup reaction and easy removal thereafter. Halides at the 5-position of quinoline were found to be much more reactive than those at the 7- and 8-positions. Finally, we have also found a unique method to reduce the pyridyl ring on quinolines, leaving a halogen substituent untouched.
Li, Jianke,Kung, Daniel W.,Griffith, David A.
scheme or table
p. 3876 - 3878
(2010/08/19)
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