Issue 2, 1988

Reduction of 1-(2-hydroxy-3,5-di-t-butylphenyl)pyridinium halides and their zwitterions. Formation of di- and tetra-hydropyrido[2,1-b]benzoxazoles

Abstract

Reduction of 1-(2-hydroxy-3,5-di-t-butylphenyl)pyridinium halides (1ad) and/or their zwitterions (2ad) with Raney Ni–Al alloy, Raney Ni (W2) and NaBH4 were investigated. When (1) was treated with Ni-Al alloy in a mixture of methanol and 30% aqueous KOH, novel cyclization products, 1,2,3,4-tetrahydro-(5ad) and 3,4-dihydro-pyrido[2,1-b]benzoxazoles (6a) and (6b) were obtained. Raney Ni catalyzed hydrogenation of (1a), (1b), (2a), (2b), and (2d) gave (5) and/or 2-piperidinophenols (4). Reduction of (1b) and (1d) with NaBH4 was re-examined and 1,2-dihydro-(7) and 1,4-dihydro-pyrido[2,1 -b]benzoxazole (8) were isolated, respectively, as byproducts.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1988, 327-331

Reduction of 1-(2-hydroxy-3,5-di-t-butylphenyl)pyridinium halides and their zwitterions. Formation of di- and tetra-hydropyrido[2,1-b]benzoxazoles

G. Fukata, T. Itoh, S. Mataka and M. Tashiro, J. Chem. Soc., Perkin Trans. 1, 1988, 327 DOI: 10.1039/P19880000327

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