Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5220462 | Tetrahedron | 2011 | 7 Pages |
Abstract
The tandem reaction of cyanoacetanilides with triflic anhydride in DMF proceeded at room temperature to afford 3-formyl-4-hydroxyquinolin-2(1H)-ones in good to high yields. A detailed mechanistic study revealed that the tandem reaction proceeded via α-dimethylaminomethylenation, which promoted the subsequent Houben–Hoesch-type cyclization. Both α-functionalization and the cyclization steps were optimized, and a multi-gram scale synthesis of 3-formyl-4-hydroxyquinolin-2(1H)-one was achieved.
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