Publication

Versatile functionalization of electron rich-fused heterocyclic arenes via electrophilic aromatic addition reaction and their applications

조회수 : 155 등록일 : 2016.10.03 00:00

저자 : Chi, DY (Chi, Dae Yoon)
출처 : TETRAHEDRON
출판일 : 2016.08.18
 
 
Versatile functionalization of electron rich-fused heterocyclic arenes via electrophilic aromatic addition reaction and their applications
 
 
Jang, KS (Jang, Keun Sam)[ 1 ] ; Shin, DS (Shin, Dong Seok)[ 2 ] ; Srisook, E (Srisook, Ekaruth)[ 3 ] ; Song, HC (Song, Ho-Chun)[ 1 ] ; Chi, DY (Chi, Dae Yoon)[ 2 ]
 
 
[ 1 ] Chonnam Natl Univ, Sch Med, Dept Nucl Med, Gwangju, South Korea
[ 2 ] Sogang Univ, Dept Chem, 35 Baekbeomro Mapogu, Seoul 04107, South Korea
[ 3 ] Burapha Univ, Dept Chem, Chon Buri 20131, Thailand

 
 
Divergent functionalized 8-methoxyquinaldines were synthesized via regioselective debromination, 1,3 bromine shift process, aromatization with treatment of a strong base, nucleophilic substitution reaction at the C7 position using amines and cyanide as a nucleophile in the absence of a metal source and a catalyst from an unusual electrophilic aromatic addition (Ad(E)Ar) reaction products 7 and 8. In addition, quinaldine-7,8-dione was prepared by presence of CAN (ceric ammonium nitrate) in AcOH and H2O for 10 min at room temperature from N-(alkylamino)-8-methoxyquinalidines. During the Ad(E)Ar reaction, new stereoselective dearomatized addition products were generated via discriminative reaction routes depending on the methoxy and bromine occupancy position. The Ad(E)Ar reaction not only allowed for the functionalization of electron rich-fused heterocyclic arenes, but also provided a new synthetic route to an alternative mechanism for electrophilic aromatic substitution reactions. (C) 2016 Published by Elsevier Ltd.
 
 
 
 
 
 
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