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.

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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

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article

Trimethylsilyl Polyphosphate Promoted Efficient Synthesis of 4(3H)‐Quinazolinones from Methyl Anthranilate

Jimena E. Díaz, Nadia Gruber, Liliana R. Orelli, Natalia B. Kilimciler et al.
2 citations
European Journal of Organic Chemistry
Quinazolinone synthesis and applications
0.50
article

Trimethylsilyl Polyphosphate Promoted Efficient Synthesis of 4(3H)‐Quinazolinones from Methyl Anthranilate

Jimena E. Díaz, Nadia Gruber, Liliana R. Orelli, Natalia B. Kilimciler, Mariana Luján Cambiaso, Emiliano Emmanuel Burin
article en
2 citations

Abstract

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.

European Journal of Organic ChemistryVol. 28(2)
Universidad de Buenos Aires (AR), Instituto de Química y Fisicoquímica Biológicas (AR)
Consejo Nacional de Investigaciones Científicas y Técnicas, Universidad de Buenos Aires, Agencia Nacional de Promoción Científica y Tecnológica
Responsible consumption and production
Openalex Percentile: Top 37%
Quinazolinone synthesis and applications
0.50
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Trimethylsilyl Polyphosphate Promoted Efficient Synthesis of 4(3<i>H)‐</i>Quinazolinones from Methyl Anthranilate — Jimena E. Díaz, Nadia Gruber, et al. · European Journal of Organic Chemistry (2024) | TGRS Research Map | TGRS