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Molecules 2007, 12(8), 2017-2028; doi:10.3390/12082017
Article

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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3, 4 and 5,*
Received: 3 June 2007 / Revised: 8 August 2007 / Accepted: 8 August 2007 / Published: 22 August 2007
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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.
Keywords: Synthesis; coumarin; 1; 2; 4-thiadiazines; fused heterocycles. Synthesis; coumarin; 1; 2; 4-thiadiazines; fused heterocycles.
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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. Molecules 2007, 12, 2017-2028.

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