Treatment of mercury(II) nicotinate with iodine and bromine in nitrobenzene at 180-185 °C for 2 h afforded 3-iodo-and 3-bromopyridines in 44% and 27% yields, respectively, without any regioisomers and dihalopyridines. From mercury(II) picolinate only 2-3% of 2-bromopyridine was obtained under similar reaction conditions, while the reaction using mercury(II) isonicotinate did not give any products. When a mixture of nicotinic acid and HgO was used in place of mercury(II) nicotinate, the halodecarboxylation occurred with similar ease. An ionic pathway involving the initial attack of electrophilic Hg(II) species on the ring-C bearing carboxyl group to afford a 3-pyridylmercury(II) compound and the subsequent replacement of the Hg(II) moiety by electrophilic iodine and bromine was proposed for this reaction.
Synthesis and pharmacological evaluation of several compounds related to 2-[2-(1-imidazolyl)ethyl]-4-(3-pyridyl)-1(2H)-phthalazinones are described. The phenyl moiety of the phthalazinone skeleton was found to play an important role in both thromboxane A2 synthetase-inhibitory and bronchodilatory activities. Further, the 3-pyridyl group at the 4-position was shown to be necessary for in vivo thromboxane A2 synthetase-inhibitory activity.
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