Pyridines 2-alkylthio-, syntheses

Drescher, M., Ohler, E., and Zbiral, E., A convenient approach to dialkyl heteroarylmethylphospho-nates and [alkylthio(heteroaryl)methyl]phosphonates. Synthesis of imidazo[l,2-a]pyridine, imi-dazo[l,2-fii]pyrimidine, indohzine and thiazole derivatives. Synthesis, 362, 1991. 

The use of 1,1,3,3-tetramethoxypropane (10) for the synthesis of 2,3-disub-stituted pyridines is further exemplified by the two-stage preparation of the 2-bromo-3-(alkylthio)pyridine (11) from (trifluoromethylthio)acetonitrile (9) (Scheme... 

Pyridine 1-oxide reacts with adamantane-1-thiol in acetic anhydride to give 2- and 3-(l-adamantanethio)pyridines and their tetrahydropyridine analogues. Corresponding butylthio-substituted pyridines are obtained using Bu SH or Bu SH in this reaction in the presence of a chloroformic acid derivative. No complications arise in the use of 3-bromopyridine 1-oxide and KSH for the synthesis of 3,3 -dipyridyl sulphide. 2-Methyl- or 2-phenyl-pyridine is converted into its 5-alkylthio-homologue by reaction of the pyridine-MeLi adduct with a dialkyl disulphide. ... 

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