THE SYNTHESIS OF RING SYSTEMS RELATED TO MORPHINE .3. 5,6-DIMETHOXY-4-CYANOMETHYL-1,2-NAPHTHOQUINONE AND ITS CONDENSATION WITH DIENES
THE SYNTHESIS OF RING SYSTEMS RELATED TO MORPHINE .3. 5,6-DIMETHOXY-4-CYANOMETHYL-1,2-NAPHTHOQUINONE AND ITS CONDENSATION WITH DIENES
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DOI：
10.1021/ja01157a064
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发表时间：
1950-01-01
影响因子：
15
通讯作者：
GATES, M
中科院分区：
文献类型：
--
作者：
GATES, M
(3) Willstátter and Parnas, Ber., 40, 1410 (1907). nitrosation of VI occurs in the 1 position and that the product of reduction and oxidation of this nitroso compound has the structure assigned VIII is afforded by the conversion of VIII to benzo [ajphenazine (XI) through the intermediate 3-benzoyloxy-(IX) and 3-hydroxy-(X) com-pounds.The quinone VIII can be reduced in high yield to the hydroquinone XII by means of sulfur dioxide and methylation of this hydroquinone with dimethyl sulfate and potassium carbonate in acetone affords 5, 6-dimethoxy-2-naphthol benzoate (XIII) in yields of 82-86%. Short alkaline hydrolysis of this benzoate followed bydistillation of the crude material yields pure 5, 6-dimethoxy-2-naphthol (XIV) in 80% yield. The steps nitrosation and conversion to the 1, 2-quinone through the aminonaphthol, described above for the monobenzoate of 2, 6-dihydroxynaphthalene, when applied to 5, 6-dimethoxy-2-naphthol produce pure 5, 6-dimethoxy-1, 2-naphthoquinone (XV). Yields for the twosteps are 97 and 89%, respectively. This quinone gives
