Tetrahedron letters

Selective ipso-substitution in pyridine ring and its application for the synthesis of macrocylces containing both oxa-and thia-bridges

N Furukawa, S Ogawa, T Kawai, S Oae

Index: Furukawa, Naomichi; Ogawa, Satoshi; Kawai, Tsutomu; Oae, Shigeru Tetrahedron Letters, 1983 , vol. 24, # 31 p. 3243 - 3246

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Citation Number: 15

Abstract

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.