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Palladium‐Catalyzed Cyclization Reaction of o ‐Haloanilines, CO 2 and Isocyanides: Access to Quinazoline‐2,4(1 H ,3 H )‐diones
Author(s) -
Zhang WenZhen,
Li Honglin,
Zeng Yang,
Tao Xueyan,
Lu Xiaobing
Publication year - 2018
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201700581
Subject(s) - chemistry , quinazoline , palladium , catalysis , medicinal chemistry , base (topology) , isocyanide , combinatorial chemistry , organic chemistry , mathematical analysis , mathematics
Quinazoline‐2,4(1 H ,3 H )‐diones are core structural subunits frequently found in many biologically important compounds. The reaction of 2‐aminobenzonitrile and CO 2 , which was frequently studied, only provided N 3‐unsubstituted quinazoline‐2,4(1 H ,3 H )‐dione compounds. Herein we report palladium‐catalyzed cyclization reactions of o ‐haloanilines, CO 2 and isocyanides to prepare N 3‐substituted quinazoline‐2,4(1 H ,3 H )‐diones. Electron‐rich o ‐bromoanilines participated in the cyclization reaction using Cs 2 CO 3 at high temperature, and electron‐deficient o ‐bromoaniline or o ‐iodoaniline substrates conducted the reaction using CsF as base to deliver corresponding quinazoline‐2,4(1 H ,3 H )‐dione products in good yields.