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

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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

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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.
License of this version: CC BY-NC-SA 3.0 Unported
Document Type: Article
Publishing status: publishedVersion
Issue Date: 2007
Appears in Collections:Naturwissenschaftliche Fakultät

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pos. country downloads
total perc.
1 image of flag of Germany Germany 48 41.38%
2 image of flag of United States United States 28 24.14%
3 image of flag of India India 10 8.62%
4 image of flag of China China 9 7.76%
5 image of flag of No geo information available No geo information available 3 2.59%
6 image of flag of Serbia Serbia 2 1.72%
7 image of flag of Netherlands Netherlands 2 1.72%
8 image of flag of Hungary Hungary 2 1.72%
9 image of flag of France France 2 1.72%
10 image of flag of Taiwan Taiwan 1 0.86%
    other countries 9 7.76%

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