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Tandem Reactions of 1,3-Diacid Chlorides with 2-Methylimidazoline and 2-Methyl-1,4,5,6-tetrahydropyrimidine: One-Pot Synthesis of 1,8-Naphthyridinetetraones

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posted on 2008-07-04, 00:00 authored by Guozhong Ye, Aihua Zhou, William P. Henry, Yingquan Song, Sabornie Chatterjee, Debbie J. Beard, Charles U. Pittman, Jr.
The reactions of 2-methylimidazoline and 2-methyl-1,4,5,6-tetrahydropyrimidine with 1,3-diacid chlorides, in the presence of Et3N in refluxing MeCN give highly functionalized potentially bioactive 1,8-naphthyridinetetraones. 2-Methylimidazoline and 2-methyl-1,4,5,6-tetrahydropyrimidine can be viewed as tridentate nucleophiles which give four consecutive tandem nucleophilic attacks on electrophiles.

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