Synthesis of a Pyrrolo[1,2-a]quinazoline-1,5-dione Derivative by Mechanochemical Double Cyclocondensation Cascade
N-heterocyclic compounds, such as quinazolinone derivatives, have significant biological activities. Nowadays, as the demand for environmentally benign, sustainable processes increases, the application of compounds from renewable sources, easily separable heterogeneous catalysts and efficient, alter...
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| Published in: | Molecules (Basel, Switzerland) Vol. 27; no. 17; p. 5671 |
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| Language: | English |
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| Abstract | N-heterocyclic compounds, such as quinazolinone derivatives, have significant biological activities. Nowadays, as the demand for environmentally benign, sustainable processes increases, the application of compounds from renewable sources, easily separable heterogeneous catalysts and efficient, alternative activation methods is of great importance. In this study, we have developed a convenient, green procedure for the preparation of 3a-methyl-2,3,3a,4-tetrahydropyrrolo[1,2-a]quinazoline-1,5-dione through a double cyclocondensation cascade using anthranilamide and ethyl levulinate. Screening of various heterogeneous Brønsted acid catalysts showed that Amberlyst® 15 is a convenient choice. By applying mechanochemical activation in the preparation of this N-heterotricyclic compound for the first time, it was possible to shorten the necessary time to three hours compared to the 24 h needed under conventional conditions to obtain a high yield of the target product. |
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| AbstractList | N-heterocyclic compounds, such as quinazolinone derivatives, have significant biological activities. Nowadays, as the demand for environmentally benign, sustainable processes increases, the application of compounds from renewable sources, easily separable heterogeneous catalysts and efficient, alternative activation methods is of great importance. In this study, we have developed a convenient, green procedure for the preparation of 3a-methyl-2,3,3a,4-tetrahydropyrrolo[1,2-a]quinazoline-1,5-dione through a double cyclocondensation cascade using anthranilamide and ethyl levulinate. Screening of various heterogeneous Brønsted acid catalysts showed that Amberlyst® 15 is a convenient choice. By applying mechanochemical activation in the preparation of this N-heterotricyclic compound for the first time, it was possible to shorten the necessary time to three hours compared to the 24 h needed under conventional conditions to obtain a high yield of the target product. N -heterocyclic compounds, such as quinazolinone derivatives, have significant biological activities. Nowadays, as the demand for environmentally benign, sustainable processes increases, the application of compounds from renewable sources, easily separable heterogeneous catalysts and efficient, alternative activation methods is of great importance. In this study, we have developed a convenient, green procedure for the preparation of 3a-methyl-2,3,3a,4-tetrahydropyrrolo[1,2- a ]quinazoline-1,5-dione through a double cyclocondensation cascade using anthranilamide and ethyl levulinate. Screening of various heterogeneous Brønsted acid catalysts showed that Amberlyst ® 15 is a convenient choice. By applying mechanochemical activation in the preparation of this N -heterotricyclic compound for the first time, it was possible to shorten the necessary time to three hours compared to the 24 h needed under conventional conditions to obtain a high yield of the target product. N-heterocyclic compounds, such as quinazolinone derivatives, have significant biological activities. Nowadays, as the demand for environmentally benign, sustainable processes increases, the application of compounds from renewable sources, easily separable heterogeneous catalysts and efficient, alternative activation methods is of great importance. In this study, we have developed a convenient, green procedure for the preparation of 3a-methyl-2,3,3a,4-tetrahydropyrrolo[1,2-a]quinazoline-1,5-dione through a double cyclocondensation cascade using anthranilamide and ethyl levulinate. Screening of various heterogeneous Brønsted acid catalysts showed that Amberlyst[sup.®] 15 is a convenient choice. By applying mechanochemical activation in the preparation of this N-heterotricyclic compound for the first time, it was possible to shorten the necessary time to three hours compared to the 24 h needed under conventional conditions to obtain a high yield of the target product. |
| Audience | Academic |
| Author | Kolcsár, Vanessza Judit Szőllősi, György |
| AuthorAffiliation | 1 Department of Organic Chemistry, Faculty of Science and Informatics, Institute of Chemistry, University of Szeged, Dóm tér 8, 6720 Szeged, Hungary 2 ELKH-SZTE, Stereochemistry Research Group, University of Szeged, Eötvös utca 6, 6720 Szeged, Hungary |
| AuthorAffiliation_xml | – name: 2 ELKH-SZTE, Stereochemistry Research Group, University of Szeged, Eötvös utca 6, 6720 Szeged, Hungary – name: 1 Department of Organic Chemistry, Faculty of Science and Informatics, Institute of Chemistry, University of Szeged, Dóm tér 8, 6720 Szeged, Hungary |
| Author_xml | – sequence: 1 fullname: Kolcsár, Vanessza Judit – sequence: 2 fullname: Sz?ll?si, György |
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| Title | Synthesis of a Pyrrolo[1,2-a]quinazoline-1,5-dione Derivative by Mechanochemical Double Cyclocondensation Cascade |
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