Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Synthesis in the Diazasteroid Group. IV. A Synthesis of 2, 3-Dimethoxy-8, 14-diaza-15-oxo-gona-1, 3, 5 (10)-triene
MASANORI NAGATASUMIKO MIYAKOSHIHIROSHI TAKEZAWAKATSUHIDE MATOBATAKAO YAMAZAKI
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1975 Volume 23 Issue 12 Pages 3056-3061

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Abstract
3, 4-Dimethoxyphenethyl hydrazine (III), reacting with ethyl γ-oxopimelate, was converted into the hydrazone (IV), which was reduced to the corresponding hydrazine (V). V was then subjected to the intramolecular ring closure to afford (VI), which showed dimorphism. VI was subjected to the Bischler-Napieralski reaction accompanied with the reduction to afford the titled compound (VIII), which was also obtained by the Bischler-Napieralski ring closure of V followed by the reduction and the ring closure to furnish the D-ring of the diazasteroid. The stereochemistry of VIII was discussed based on its nuclear magnetic resonance data and its mercuric acetate oxidation.
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© The Pharmaceutical Society of Japan
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