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Communication | Regular issue | Vol 43, No. 6, 1996, pp.1151-1158
Published online, 1st January, 1970
DOI: 10.3987/COM-96-7397
Oxidation of Substituted Pyridines PyrCHRSiMe3 (R=H, Me, Ph) and Substituted Quinolines QnCH2SiMe3 with Hypervalent Iodine Reagents

Ian P. Andrews,* Norman J. Lewis, Alexander McKillop, and Andrew S. Wells

*SmithKline Beecham Pharmaceuticals R &D, Old Powder Mills, nr. Leigh, Tonbridge, Kent, TN11 9AN, U.K.

Abstract

Oxidation of a variety of substituted pyridines PryCHRSiMe3 (R=H, Me, Ph) and quinolines, QnCH2SiMe3 with hypervalent iodine reagents PIDA, (PhI(OCOCH3)2) and PIFA, (PhI(OCOCF3)2) has been studied. Oxy-desilylation with PIDA/TBAF gives low to moderate yields of PyrCHROR1 and QnCH2OR1 (R1=H,Ac), while good yields of PyrCHROH and QnCH2OH are obtained when PIFA is used.