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Synthesis 2024; 56(09): 1485-1497
DOI: 10.1055/a-2243-4727
DOI: 10.1055/a-2243-4727
paper
Synthesis of Thiazole-fused Tricyclic Quinazolinone Alkaloids and Their Derivatives
This work was partially supported by the Université de Rouen, Normandy, the Institut National des Sciences Appliquées Rouen (INSA Rouen Normandy), the Centre National de la Recherche Scientifique (CNRS), the European Regional Development Fund (ERDF), Labex SynOrg (ANR-11-LABX-0029), Carnot Institute I2C, the XL-Chem Graduate School of Research (ANR-18-EURE-0020 XL CHEM), and the Région Normandie. N.B. thanks the Ministère de l’Enseignement supérieur, de la Recherche et de l’Innovation (MESRI) for a PhD grant. C.L. thanks the XL-Chem Graduate School of Research for a grant.
Abstract
The synthesis of thiazole-fused derivatives of tricyclic quinazolinones hitherto undescribed was successfully achieved by replacing anthranilic acid or its derivatives by isomeric polyfunctionalized benzothiazole analogues of anthranilic methyl esters. Some of the new heterocyclic systems are inspired by natural alkaloids such as mackinazolinone, deoxyvasicinone, and isaindigotone, showing interesting biological properties. The microwave-assisted method developed is a variant of the Niementowski reaction and was also applied to the synthesis of ring-extended rutaecarpine derivatives.
Key words
2,3-fused quinazolinones - mackinazolinone - deoxyvasicinone - isaindigotone - rutaecarpine - 2-cyanobenzothiazole - benzothiazole - Niementowski reactionSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2243-4727.
- Supporting Information
Publication History
Received: 20 December 2023
Accepted after revision: 11 January 2024
Accepted Manuscript online:
11 January 2024
Article published online:
12 February 2024
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