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A facile synthesis of substituted 3-amino-1H-quinazoline-2,4-diones

โœ Scribed by Tuan P. Tran; Edmund L. Ellsworth; Brian M. Watson; Joseph P. Sanchez; H. D. Hollis Showalter; John R. Rubin; Michael A. Stier; Judy Yip; Dai Q. Nguyen; Paul Bird; Rajeshwar Singh

Publisher
Journal of Heterocyclic Chemistry
Year
2005
Tongue
English
Weight
124 KB
Volume
42
Category
Article
ISSN
0022-152X

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โœฆ Synopsis

A new synthesis of a series of 3-amino-1H-quinazoline-2,4-diones is described. The 1H-quinazoline-2,4dione 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.

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ChemInform Abstract: Solid-Phase Synthes
ChemInform Abstract: Solid-Phase Synthesis of Chiral 3-Substituted Quinazoline-2,4-diones.
โœ L. GOUILLEUX; J.-A. FEHRENTZ; F. WINTERNITZ; J. MARTINEZ ๐Ÿ“‚ Article ๐Ÿ“… 2010 ๐Ÿ› John Wiley and Sons โš– 29 KB ๐Ÿ‘ 1 views

Solid-Phase Synthesis of Chiral 3-Substituted Quinazoline-2,4-diones. -A series of N-urethane precursors such as (I) or (III) are prepared and subjected to cyclization in the presence of base (DBU, NaOH or NEt3). The desired quinazolines are obtained in good to excellent yield without racemization.