The Reaction of Heteroaromatic N-Oxide with Acid Chloride and Cyanide. VII. On the Reaction of Pyridine 1-Oxides with Sulfonic Acid Chloride and Potassium Cyanide

Abstract

Reaction of pyridine 1-oxide (I) with sulfonic acid chloride (RSO₂Cl) and potassium cyanide was carried out. Application of methanesulfonyl chloride or ethanesulfonyl chloride afforded 2-methyl- or 2-ethyl-sulfonylpyridine (IIm or IIe) and 4-methyl- or 4-ethyl-sulfonylpyridine (IVm or IVe). Application of benzenesulfonyl chloride or p-toluenesulfonyl chloride gave 3-phenyl- or p-tolyl-sulfonylpyridine (IIIb or IIIt) and 4-phenyl- or p-tolyl-sulfonylpyridine (IVb or IVt), with 2-pyridinecarbonitrile (I_1') at the same time. Application of methanesulfonyl chloride and potassium cyanide to 2- (I₁), 3- (I₂), and 4-pyridinecarbonitrile 1-oxide (I₃), and 4-chloropyridine 1-oxide (I₄) resulted in the formation of 2-methylsulfonyl substituted compounds in all cases. In the case of I₂, 4-methylsulfonyl derivative was also formed in a minute amount.