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Synthesis of Fused Isoquinolinone and Iminoisoindolinone Derivatives via a Copper‐Catalyzed Regioselective Switching Process
Author(s) -
Kavala Veerababurao,
Wang ChengChuan,
Wang YuHsuan,
Kuo ChunWei,
Janreddy Donala,
Huang WenChang,
Kuo TingShen,
He Chiu Hui,
Chen MeiLing,
Yao ChingFa
Publication year - 2014
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.201301105
Subject(s) - chemistry , regioselectivity , nucleophile , combinatorial chemistry , cyanide , substrate (aquarium) , catalysis , functional group , amine gas treating , derivative (finance) , stereochemistry , organic chemistry , oceanography , polymer , financial economics , economics , geology
Copper‐catalyzed base switching procedures for the synthesis of various fused isoquinolinone derivatives and iminoisoindolinone derivatives from the same starting materials have been developed. In these reaction sequences it is found that benzyl cyanide acts as a nucleophile in the presence of strong bases while it acts as a cyanide donor in the presence of weak bases. A wide substrate scope, good functional group tolerance, and handy reaction conditions are the important features of these protocols. Futhermore, using these protocols a wide variety of imidazolone‐fused isoquinolinone derivatives, pyrimidinone‐fused isoquinolinone derivatives, a diazapinone‐fused isoquinolinone derivative and iminoisoindolinone derivatives were accessed in excellent to moderate yields.