Regiocontrolled Nitration of 4-Quinolones at Ambient Conditions

Abstract

Regiocontrolled nitration of 4-quinolone, the highly privileged scaffold, has been developed at ambient conditions. The nitro group can selectively be introduced at diverse positions simply by tuning the reactivity of the moiety. Discrimination is being achieved through the selective functionalization of the free N-H group. The functional group has been screened theoretically with the help of Fukui function and local softness calculation. Theoretical predictions are synchronized well with the experimental findings. Finally, this nitration technique allows quick access to the structurally diverse 4-quinolones.

GRAPHICAL ABSTRACT

Keywords:

• Ambient conditions
• Fukui function
• local softness
• 4-quinolones
• regiocontrolled nitration

Supplemental Material

Supplemental data for this article can be accessed on the publisher’s website.