1. ChemInform Abstract: Reactivity and Regioselectivity in the Acylation of 2,4-Diaminoquinazolines
- Author
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M. Fernanda R. P. Proença and Elina Margarida Ribeiro Marinho
- Subjects
chemistry.chemical_classification ,010405 organic chemistry ,Chemistry ,Substituent ,Regioselectivity ,General Medicine ,010402 general chemistry ,01 natural sciences ,Medicinal chemistry ,0104 chemical sciences ,Acylation ,chemistry.chemical_compound ,Acetic anhydride ,Aniline ,Heterocyclic amine ,Reactivity (chemistry) ,Acyl group - Abstract
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.
- Published
- 2016