Please use this identifier to cite or link to this item: http://hdl.handle.net/1822/51950

TitleReactivity and regioselectivity in the acylation of 2,4-diaminoquinazolines
Author(s)Marinho, Elina Margarida Ribeiro
Proença, M. Fernanda R. P.
KeywordsAcyl chlorides
Isocyanates
Anhydrides
Acylation
4-aminoquinazolines
Issue date2016
PublisherElsevier
JournalTetrahedron
Abstract(s)2-(2-Aminophenyl)quinazoline-4-amines were selectively acylated at the phenylamino group by anhydrides, isocyanates or acyl chlorides, at room temperature. A similar selectivity was obtained in the reaction with ethoxymethylene derivatives and orthoesters. Acylation of the exocyclic imino substituent in the quinazolino-quinazoline tetracyclic structure also occurred under mild conditions with acetic anhydride and isocyanates. Hydrolysis to release the aniline substituent was performed with concd HCl (1 equiv at 60 °C) and with 3 M NaOH (3 equiv, rt), leading to the formylated derivative or cleaving the acyl group in the heterocyclic amine.
TypeArticle
URIhttp://hdl.handle.net/1822/51950
DOI10.1016/j.tet.2016.06.003
ISSN0040-4020
Publisher versionhttps://www.sciencedirect.com/science/article/pii/S0040402016305075
Peer-Reviewedyes
AccessRestricted access (UMinho)
Appears in Collections:CDQuim - Artigos (Papers)

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