Trimethylsilyl Polyphosphate Promoted Efficient Synthesis of 4(3<i>H)‐</i>Quinazolinones from Methyl Anthranilate
Abstract A trimethylsilyl polyphosphate (PPSE) promoted synthesis of 4(3 H )‐quinazolinones, a heterocycle with wide biological potential, from methyl anthranilate and secondary amides is described. The procedure is general, involves very easily available starting materials, shows functional group tolerance and leads to good to excellent yields. The method proved to be suitable for scaling‐up. A one‐pot approach was also explored. This step‐economic modification reduces the time, waste and environmental impact of the synthesis and leads to satisfactory global yields that include 2 or 3 single steps. Finally, a possible reaction mechanism that involves a nitrilium cation intermediate is proposed.
Authors
- Jimena E. Díaz
- Nadia Gruber
- Liliana R. Orelli
- Natalia B. Kilimciler
- Mariana Luján Cambiaso
- Emiliano Emmanuel Burin
Institutions
- Universidad de Buenos Aires (AR)
- Instituto de Química y Fisicoquímica Biológicas (AR)
Publication Details
- Journal
- European Journal of Organic Chemistry
- Published
- 2024-12-23
- DOI
- https://doi.org/10.1002/ejoc.202401012
- Citations
- 2
- Primary Topic
- Quinazolinone synthesis and applications
- Type
- article
- Field-Weighted Citation Impact
- 0.50
Funders
- Consejo Nacional de Investigaciones Científicas y Técnicas
- Universidad de Buenos Aires
- Agencia Nacional de Promoción Científica y Tecnológica