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.
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.
Jashari
Ahmed
A
Group of Physics and Chemistry, Faculty of Natural Sciences and Mathematics, State University of Tetova, 1200 Tetova, Macedonia. ahmed_alban@yahoo.com
Hey-Hawkins
Evamarie
E
Mikhova
Bozhana
B
Draeger
Gerald
G
Popovski
Emil
E
D000631:Aminopyridines / Q000737:chemistry; D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D001578:Benzopyrans / Q000138:chemical synthesis* / Q000737:chemistry; D003374:Coumarins / Q000138:chemical synthesis* / Q000737:chemistry; D013450:Sulfones / Q000138:chemical synthesis* / Q000737:chemistry; D013844:Thiazoles / Q000737:chemistry
C524608:4-chlorocoumarin-3-sulfonyl chloride; D000631:Aminopyridines; D019380:Anti-HIV Agents; D000970:Antineoplastic Agents; D001578:Benzopyrans; D003374:Coumarins; D013450:Sulfones; D013844:Thiazoles