Publicação
Reactivity and regioselectivity in the acylation of 2,4-diaminoquinazolines
| Resumo: | 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. |
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| Autores principais: | Marinho, Elina Margarida Ribeiro |
| Outros Autores: | Proença, M. Fernanda R. P. |
| Assunto: | Acyl chlorides Isocyanates Anhydrides Acylation 4-aminoquinazolines |
| Ano: | 2016 |
| País: | Portugal |
| Tipo de documento: | artigo |
| Tipo de acesso: | acesso restrito |
| Instituição associada: | Universidade do Minho |
| Idioma: | inglês |
| Origem: | RepositóriUM - Universidade do Minho |
| Resumo: | 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. |
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