Abstract Both the sulfinyl and sulfonyl groups directly bound to 2 or 4 position in pyridine were readily displaced by several nucleophiles such as RO-and RS-. The facility of the leaving groups is RSO 2⋍ RSO> Br⋍>> RS (R: alyl or benzyl). The ipso-substituion could be applied for the synthesis of new type of 2, 6-disubstituted macrocycles containing both carbonoxygen and carbon-sulfur bridges in moderate yields.