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Traceless synthesis of quinazoline‐2,4‐diones by curtius rearrangement reaction using poly(ethylene glycol) as soluble polymeric support
Author(s) -
Huang Yanling,
Lu Cuifen,
Chen Zuxing,
Yang Guichun
Publication year - 2007
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570440628
Subject(s) - curtius rearrangement , chemistry , ethylene glycol , azide , quinazoline , peg ratio , cleavage (geology) , combinatorial chemistry , ethylene , organic chemistry , polymer chemistry , catalysis , geotechnical engineering , finance , fracture (geology) , engineering , economics
We have developed an efficient method to synthesize various quinazoline‐2,4‐diones using poly‐(ethylene glycol) as soluble polymeric support. The procedure of this reaction included: formation of acyl azide, efficient Curtius rearrangement, nucleophlic addition with amines to produce ureas, cyclization and concurrent cleavage of the resulted six‐membered heterocycle from PEG‐support in excellent yields. This method is mild and manipulation is easy.