Synthesis of 1-Alkyl-1,2,3,4,6,7-hexahydro-11bH-benzo [a] quinolizin-2-one Derivatives.

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概要

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• A new synthesis of 1-alkyl-9,10-dimethoxy-1,2,3,4,6,7-hexahydro-11bH-benzo [a] quinolizin-2-ones (VIII) (5 specimens) was described. 3-(3,4-Dimethoxyphenethylamino) propionitrile was acylated with the chloride of various ethyl alkylhydrogenmalonates followed by esterification to yield the corresponding diester-amides (V), which were cyclized by refluxing with phosphoryl chloride alone. The products were reduced to afford α-alkyl-2-(2-ethoxycarbonylethyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-1-isoquinoline acetates (VI). The latter were cyclized with sodium hydride in boiling toluene according to Dieckmann's method and the products were submitted to ketonic fission to yield the ultimate products in rather a poor yield. 6,7-Dimethoxy-3,4-dihydroisoquinoline was the common by-product produced during the ketonic fission reaction.

• 公益社団法人日本薬学会の論文
• 1962-03-25

著者

• 川西 正純

  Organic Chemistry Research Laboratry Tanabe Seiyaku Co. Ltd.

• 川西 正純

  Tokyo Research Laboratory, Tanabe Seiyaku Co., Ltd.

関連論文

• On the Structure of So-called Rotundine
• Synthesis of the So-called Dehydro-rotundinium Salt and Its Partial Reduction.
• Synthesis of 1-Alkyl-1,2,3,4,6,7-hexahydro-11bH-benzo [a] quinolizin-2-one Derivatives.

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