Jashari, A.; Hey-Hawkins, E.; Mikhova, B.; Draeger, G.; Popovski, E.: An improved synthesis of 4-chlorocoumarin-3-sulfonyl chloride and its reactions with different bidentate nucleophiles to give pyrido[1′, 2′:2,3]- and thiazino[3′,2′:2,3]-1,2,4-thiadiazino[6,5-c] benzopyran-6-one 7,7-dioxides. In: Molecules 12 (2007), Nr. 8, S. 2017-2028. DOI:
https://doi.org/10.3390/12082017
Abstract: |
An improved synthetic method affording 4-chlorocoumarin-3-sulfonyl chloride (4) in very good yield (ca. 85 %) is reported. This compound was reacted with various bidentate nucleophiles such as 2-aminopyridines and 2-aminothiazoles in order to obtain substituted pyrido- and thiazino-1,2,4-thiadiazino-benzopyranone dioxides (potential anticancer and anti-HIV agents). These reactions occurred rapidly at room temperature giving yellowish precipitates, which are insoluble in common organic solvents, making the purification process challenging. Further investigation has shown that these fused heterocycles are not stable and decompose with opening of the 1,2,4-thiadiazine ring. © 2007 by MDPI.
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License of this version: |
CC BY-NC-SA 3.0 Unported - https://creativecommons.org/licenses/by-nc-sa/3.0/
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Publication type: |
Article |
Publishing status: |
publishedVersion |
Publication date: |
2007 |
Keywords english: |
1,2,4-thiadiazines, Coumarin, Fused heterocycles, Synthesis, 4 chlorocoumarin 3 sulfonyl chloride, 4-chlorocoumarin-3-sulfonyl chloride, aminopyridine derivative, anti human immunodeficiency virus agent, antineoplastic agent, benzopyran derivative, coumarin derivative, sulfone, thiazole derivative, unclassified drug, article, chemistry, synthesis, Aminopyridines, Anti-HIV Agents, Antineoplastic Agents, Benzopyrans, Coumarins, Sulfones, Thiazoles
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DDC: |
540 | Chemie
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