Year 2007, Month 12 (Section Full Articles, Page 2466)
Synthesis of benzî[g]quinoline-5,10-diones
E. A. Kolodina, N. I. Lebedeva, and M. S. Shvartsberg
Addition of HCl to 2-amino-3-(4-methyl-3-oxopentynyl)-1,4-naphthoquinone in CHCl3 at 20 °Ñ is followed by its cyclization to 4-chloro-2-isopropylbenzî[g]quinoline-5,10-dione. Chlorine atom in this compound can be easily replaced by dialkylamino group upon treatment with secondary amines. 4-Dialkylamino-2-isopropylbenzî[g]quinoline-5,10-dione is also formed by the direct reaction of the starting ketone with secondary amines. Syntheses of 2-amino-3-(4-methyl-3-oxopentynyl)-1,4-naphthoquinone from 2-bromo- and 2-amino-3iodo-1,4-naphthoquinones are also described.
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