Efficient synthesis of quinoxaline derivatives by selective modification of 3-chloro-6-fluoroquinoxalin-2(1H)-one 4-oxide

Article abstract of DOI:10.1002/ejoc.201201569

The readily available and polyfunctionalized 3-chloro-6-fluoroquinoxalin- 2(1H)-one 4-oxide, derived from the efficient one-step annulation reaction of 1,1,2-trichloro-2-nitroethene with 4-fluoroaniline, was selectively modified at the chloronitrone and the amide units, leading to more than 30 new quinoxaline derivatives with a unique substitution pattern in good to excellent yields. In addition, the electronic properties of the versatile starting compound were computed by means of density functional theory, which gave a reasonable explanation for its unique reactivity. The antimalarial activity of all hitherto unknown compounds has been investigated. The polyfunctionalized 3-chloro-6-fluoroquinoxalin-2(1H)-one 4-oxide was selectively modified at the chloronitrone and the amide units. More than 30 new quinoxaline derivatives with a unique substitution pattern were synthesized in good to excellent yields. In addition, their antimalarial activity was screened. Copyright