Chemo-selective Suzuki–Miyaura reactions: Synthesis of highly substituted [1,6]-naphthyridines

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The Suzuki-Miyaura reaction of methyl-5-bromo-8-(tosyloxy)-1,6-naphthyridine-7-carboxylate(5),with 2 equiv. of arylboronic acids gave diarylated product, 5,8–diaryl-1,6-naphthyridine-7-carboxylate(7), whereas 1 equiv. of arylboronic acid resulted in site-selective formation of 5-aryl-8-(tosyloxy)-1,6-naphthyridine-7-carboxylate(8). The reactions proceeded with excellent chemo-selectivity in favor of the bromide group. Likewise, one-pot reaction with completely different boronic acids by sequential addition produced 1,6-naphthyridine-7-carboxylates,(10) containing two different aryl groups at 5 and 8 positions. The Suzuki-Miyaura reaction of methyl-5-bromo-8- (tosyloxy) -1,6-naphthyridine-7-carboxylate with 5 equiv. Of arylboronic acids gave diarylated product, 6-naphthyridine-7-carboxylate (7), while 1 equiv. Of arylboronic acid resulted in site-selective formation of 5-aryl-8- (tosyloxy) -1,6-naphthyridine- proceeded with excellent chemo-selectivity in favor of the bromide group. (one), with one-pot reaction with completely different boronic acids by sequentially added 1,6-naphthyridine-7-carboxylates, (10) containing two different aryl groups at 5 and 8 positions.
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