Synthesis of C-6 and C-3 substituted chalcogen derivatives of 2-methoxypyridine through lithiation of 2-methoxypyridine: An experimental and quantum chemical study

A methodology which can be tailored to incorporate a chalcogen atom at the C-6 or C-3 position of 2-methoxypyridine (1) was developed. The reactions of the BF3 complexed 1 with LDA and subsequently with chalcogen and iodomethane furnished a C-6 substituted product. However, the use of uncomplexed 1 afforded a C-3 substituted product.