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A Tandem Ring Opening/Closure Reaction in A BF 3 ‐Mediated Rearrangement of Spirooxindoles
Author(s) -
Guo Xuliang,
Xing Qingyu,
Lei Kunhua,
ZhangNegrerie Daisy,
Du Yunfei,
Zhao Kang
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201700728
Subject(s) - chemistry , moiety , tandem , ring (chemistry) , cascade reaction , rearrangement reaction , stereochemistry , closure (psychology) , aryl , cope rearrangement , medicinal chemistry , catalysis , organic chemistry , materials science , alkyl , economics , market economy , composite material
Treatment of the readily accessible spiro‐cyclohexadienones from the PhI(OCOCF 3 ) 2 ‐mediated spiro‐cyclization of N‐substituted benzanilides, with BF 3 ⋅Et 2 O initiates a tandem ring opening/closure reaction leading to the formation of the biologically interesting 8‐hydroxy‐phenanthridin‐6(5 H )‐one compounds. This unique rearrangement pattern involves the ‘migration’ of the electron‐deficient N ‐methyl carbamoyl moiety rather than the electron‐rich aryl group as observed and reported previously in all other similar transformations.