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New methods for functionalization of 1-methyl-2-quinolone (MeQone) skeleton are provided. The reaction of 1-methyl-3,6,8-trinitro-2-quinolone (TNQ) with amines affords quinolone dimer 1 and 6,8-dinitroquinolone (6,8-DNQ). Dimerization predominantly proceeds at room temperature, and denitration takes place under heated and diluted conditions. We also provide a plausible mechanism for these reactions...
Gentle generation of nitrile oxide bearing a carbamoyl group was performed. 4-Nitro-3-isoxazolin-5-one was treated with dipolarophiles in the mixed solvent (MeCN / H 2 O) at room temperature to afford cycloadducts in good yields.
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