Syntéza 3-fenyl-5-hydroxy-2H-1,3-benzoxazin-2,4(3H)-dionů a jejich sirných analogů

• Main Author: Růžková, Barbora
• Other Authors: Macháček, Miloš
• Format: Dissertation
• Language: Czech
• Published: 2008
• Online Access: http://www.nusl.cz/ntk/nusl-292583

Synthesis of 5-hydroxy-3-phenyl-2H-1,3-benzoxazine-2,4(3H)-diones and their sulfur analogues Barbora Růžková The thesis is concerned with the preparation of 5-hydroxy-3-phenyl-2H-1,3-benzoxazine- 2,4(3H)-diones, 5-hydroxy-3-phenyl-4-thioxo-2H-1,3-benzoxazin-2-ones and 5-hydroxy-3- phenyl-2H-1,3-benzoxazine-2,4(3H)-dithiones, i.e. cyclic analogues of 2,6-di- hydroxybenzanilides. The starting 2,6-dihydroxybenzanilides were synthesized by the microwave-assisted reaction of 2,6-dihydroxybenzooic acid with aniline (unsubstituted or para-substituted by chlorine, methyl, butyl or methoxy groups) in the presence of phosphorus trichloride. Their treatment with ethyl-chloroformate afforded 5-hydroxy-3-phenyl-2H-1,3-benzoxazine-2,4(3H)- diones in 77 - 94 % yields. 5-Hydroxy-3-phenyl-4-thioxo-2H-1,3-benzoxazin-2-ones and 5- hydroxy-3-phenyl-2H-1,3-benzoxazine-2,4(3H)-dithiones were obtained by thionation using Lawesson's reagent in 31 - 42 and 24 - 33 % yields, respectively. All the compounds were characterized by infrared and NMR spectroscopy and by elemental analysis. No substance exerted either antimycotic activity (against Candida albicans, C. tropicalis, C. krusei, C. glabrata, Trichosporon asahii, Trichophyton mentagrophytes, Aspergillus fumigates, and Absidia corymbifera) or antimycobacterial activity...