SELECTIVE IPSO-SUBSTITUTION IN PYRIDINE RING AND ITS APPLICATION FOR THE SYNTHESIS OF MACROCYCLES CONTAINING BOTH OXA- AND THIA-BRIDGES

Article abstract of DOI:10.1016/S0040-4039(00)88146-0

Both the sulfinyl and sulfonyl groups directly bound to 2 or 4 position in pyridine were readily displaced by several nucleophiles such as RO(1-) and RS(1-) .The facility of the leaving groups is RSO2 = RSO > Br = Cl >> RS (R:alkyl or benzyl).The ipso-substitution could be applied for the synthesis of new type of 2,6-disubstituted macrocycles containing both carbon-oxygen and carbon-sulfur bridges in moderate yields.