Direct amino-halogenation and aziridination of the 2-quinolone framework by sequential treatment of 3-nitro-2-quinolone with amine and N-halosuccinimide

The sequential treatment of 3-nitro-2-quinolones with amines and N-halosuccinimides under mild conditions facilitated the direct amino-halogenation and aziridination at the 4- and 3-positions of the 2-quinolone framework. The selectivity of the functionalization was influenced by the electronic properties of the substituents on the benzene moiety of the nitroquinolone. The electron-withdrawing nitro group promoted the amino-halogenation, and replacement of the nitro group with a halogen or hydrogen markedly increased the selectivity of the aziridination. Moreover, a succinimide group instead of an alkylamino group was introduced at the 4-position, affording the masked form of the 4-amino-3-chloro-2-quinolone derivative. Furthermore, the prepared bis-functionalized quinolones were subjected to Suzuki-Miyaura coupling reaction, ring opening, and hydrazinolysis to afford differently functionalized quinolones.

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