Polysubstitutsd pyridines have been prepared in fair yields by a one-step reaction of heteroarene 3-bromo-2.3-dimethaxy-5-(methoxymethyl)pyidie3 and lithio alkyl-and lithio aryl-acetonitriles via the heteroaryne 13 generated from 3 by LDA in THF.Most lithio arylacetonitriles 4a-f yield rearranged products 5a-f by ths tandem~addition rearrangement pathway and a 2:l to 3:t mixture of normal hetaryne products 6a-f and 7a-1.The other nitrlles 49-1 give mixtures 01 the usual hetaryne products in ratios of 3:l to 4 : l .6g-1:7g-1, respectively.
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Biehl et al. (1990) studied this question.