The sodium borohydride reduction of N-sulfonylpyridinium salts. Synthesis of N-sulfonyl-1,4-(1,2-) dihydropyridines

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Abstract
Reaction of alkyl (aryl) sulfonyl chlorides and sulfonic acid anhydrides with pyridine in the presence of sodium borohydride afford N-sulfonyl-1,4-dihydropyridines (1) and N-sulfonyl-1,2-dihydropyridines (2). The ratio of products (1:2) was dependent upon solvent and temperature. Reaction of 2d with 4-phenyl-1,2,4-triazoline-3,5-dione (4) afforded the endo-adduct 5.

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