87512-13-8Relevant academic research and scientific papers
SELECTIVE IPSO-SUBSTITUTION IN PYRIDINE RING AND ITS APPLICATION FOR THE SYNTHESIS OF MACROCYCLES CONTAINING BOTH OXA- AND THIA-BRIDGES
Furukawa, Naomichi,Ogawa, Satoshi,Kawai, Tsutomu,Oae, Shigeru
, p. 3243 - 3246 (1983)
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.
ipso-Substitution of a Sulphinyl or Sulphonyl Group Attached to Pyridine Rings and its Application for the Synthesis of Macrocycles
Furukawa, Naomichi,Ogawa, Satoshi,Kawai, Tsutomu,Oae, Shigeru
, p. 1839 - 1845 (2007/10/02)
A sulphinyl or sulphonyl group directly bound to the 2- or 4-position of a pyridine ring was readily displaced by several nucleophiles such as RO-, RS-, and CN- to afford the corresponding ipso-substitution products.Similarly, 2-halogeno-6-methylsulphinyl- or -methylsulphonyl-pyridines also react with nuclephiles to afford 2-halogeno-6-substituted pyridine derivatives.Thus, the leaving abilities of the leaving groups fall in the order RSO2 > RSO > Br ca.Cl >> RS (R = alkyl or benzyl).The ipso-substitution can be applied to the synthesis of 2,6-disubstituted pyridino macrocycles containing both carbon-oxygen and carbon-sulphur bridges, resulting in several new macrocycles in moderate yields.
