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Palladium‐Catalyzed 5‐ exo‐dig Cyclization Cascade, Sequential Amination/Etherification for Stereoselective Construction of 3‐Methyleneindolinones
Author(s) -
Zuo Youpeng,
He Xinwei,
Tang Qiang,
Hu Wangcheng,
Zhou Tongtong,
Hu Wenbo,
Shang Yongjia
Publication year - 2021
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.202001369
Subject(s) - chemistry , amination , stereoselectivity , intramolecular force , oxindole , catalysis , palladium , cascade , functional group , dig , protecting group , combinatorial chemistry , cascade reaction , stereochemistry , medicinal chemistry , organic chemistry , alkyl , polymer , computer security , chromatography , computer science
An cascade intramolecular 5‐ exo‐dig cyclization of N ‐(2‐iodophenyl)propiolamides and sequential amination/etherification (with N ‐hydroxybenzamides, phenyl hydroxycarbamate) protocol for the synthesis of amino‐ and phenoxy‐substituted 3‐methyleneindolinones using unexpensive Pd(PPh 3 ) 4 as catalyst has been developed. The protocol enables the assembly of structurally important oxindole cores featuring moderate functional group tolerance (particularly the halo group), affording a broad spectrum of products with diverse substituents in good to excellent yields.