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Bis(cycloocta‐1,5‐diene)nickel‐Catalyzed Carbon Dioxide Fixation for the Stereoselective Synthesis of 3‐Alkylidene‐2‐indolinones
Author(s) -
Miao Bukeyan,
Zheng Yangguangyan,
Wu Penglin,
Li Suhua,
Ma Shengming
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.201700086
Subject(s) - chemistry , stereoselectivity , nickel , carbon fixation , catalysis , diene , natural product , stereochemistry , medicinal chemistry , combinatorial chemistry , organic chemistry , carbon dioxide , natural rubber
A bis(cycloocta‐1,5‐diene)nickel‐catalyzed highly regio‐ and ( E )‐stereoselective hydrocarboxylation of 2‐alkynylanilines under very mild conditions has been developed to afford ( E )‐[2‐( o ‐aminophenyl)]acrylic acids, which could easily be converted to ( E )‐3‐alkylidene‐2‐indolinones with important potential bioactivity. The stereoselective syntheses of two biologically active molecules, ( E )‐3‐benzylidene‐2‐indolinone (chemo‐preventive potential in inducing NQO1 activity) and ( E )‐3‐(3‐methylbutylidene)‐2‐indolinone (a natural product isolated from Cimicifuga foetida with cytotoxic activity against HL‐60 cells) are presented as examples.