Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
8, 13a-Propanoberbines. III. Reaction of Acetoneberberine Type Enamine with Alkyl Halide
SHUNSUKE NARUTOHARUKI NISHIMURAHIDEHIKO KANEKO
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1975 Volume 23 Issue 6 Pages 1271-1275

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Abstract
The reaction of acetoneberberine (I) with methyl iodide was found to give 8, 13a-(2'-oxopropano)-13, 13-dimethylberbine derivative (IV) and 8, 13a-(2'-oxopropano)-13-methylberbine derivative (V) as side products together with the expected 13-methyl-berberinium (II) and berberinium iodide (III). Analogous reaction of I with allyl bromide gave rise to 8, 13a-(2'-oxopropano)-13, 13-diallylberbine derivative (XI). The structures of products were deduced from chemical and spectral data.
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© The Pharmaceutical Society of Japan
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