Synthesis of novel 2,3-substituted quinazolin-4-ones by condensation of alkyl or aromatic diamines with 5-(N-arylimino)-4-chloro-5H-1,2,3-dithiazoles |
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Authors: | Maria de Fatima Pereira |
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Affiliation: | Laboratoire de Biotechnologies et de Chimie Bio-organique, FRE CNRS 2766, UFR Sciences Fondamentales et Sciences pour l'Ingénieur, Bâtiment Marie Curie, Université de La Rochelle, F-17042 La Rochelle cedex 1, France |
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Abstract: | The work described in this paper is a further example of the utility of Appel's salt in the conception of novel heterocyclic rings. We confirmed that primary alkyldiamines may react easily with the methyl N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-anthranilates to afford quinazolines, which are very interesting starting materials for the access to novel 2,3-condensed quinazolin-4-ones. On the other side, aromatic amines allow the synthesis of polycyclic molecules, which are structurally close to the model natural products (e.g., rutaecarpine, luotonine, tryptanthrine and vasicinone). |
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Keywords: | 4,5-Dichloro-1,2,3-dithiazolium chloride (Appel's salt) Quinazolin-4-ones Alkanediamines Imino-1,2,3-dithiazoles |
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