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A facile synthesis of substituted 3‐amino‐1 H ‐quinazoline‐2,4‐diones
Author(s) -
Tran Tuan P.,
Ellsworth Edmund L.,
Watson Brian M.,
Sanchez Joseph P.,
Showalter H. D. Hollis,
Rubin John R.,
Stier Michael A.,
Yip Judy,
Nguyen Dai Q.,
Bird Paul,
Singh Rajeshwar
Publication year - 2005
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.5570420428
Subject(s) - chemistry , quinazoline , moiety , nucleophile , intramolecular force , reagent , ring (chemistry) , hydroxylamine , combinatorial chemistry , urea , medicinal chemistry , stereochemistry , organic chemistry , catalysis
A new synthesis of a series of 3‐amino‐1 H ‐quinazoline‐2,4‐diones is described. The 1 H ‐quinazoline‐2,4‐dione 10 was made starting with fluorobenzoic acid in three high yielding steps. The key step of this synthesis involved the generation of the dianion of urea 7 and the subsequent intramolecular nucleophilic displacement of the 2‐fluoro to form the quinazolinedione ring. The 3‐amino moiety was incorporated using (2,4‐dinitro‐phenyl)‐hydroxylamine as the aminating reagent.