Synthesis of 2-Formylazulene and Its Derivatives by Oxidative Cleavage of 2-Styrylazulenes
Synthesis of 2-Formylazulene and Its Derivatives by Oxidative Cleavage of 2-Styrylazulenes
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2-苯乙烯基薁烯氧化裂解合成2-甲酰基薁烯及其衍生物
DOI：
10.1246/bcsj.53.3696
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发表时间：
1980
影响因子：
4
通讯作者：
K. Takase
中科院分区：
文献类型：
--
作者：
M. Saito;T. Morita;K. Takase
用NaIO_4-−-OsO_4氧化裂解苯并咪唑烯，合成了2-甲酰偶氮烯及其衍生物。合成了1，2-二甲酰基-天青烯、1，2，3-三甲酰天青烯和5-甲酰天青烯衍生物。2-甲基偶氮唑烯-1，3-二羧酸二甲酯与对亚硝基-N，N-二甲基苯胺在NaOR(R=Me或Et)存在下反应生成相应的3-alkoxycarbonyl-2-[p-(dimethylamino)phenyliminomethyl]azulene-1-carboxylic酸，再用盐酸水解得到3-烷氧基甲酰基-2-甲酰基偶氮唑烯-1-羧酸。2-甲酰基偶氮烯-1-羧酸与乙酸酐进行乙酰化反应，得到五元乳酸乙酸酯。
2-Formylazulene and its derivatives were prepared by the oxidative cleavage of styrylazulenes with NaIO4−OsO4. 1,2-Diformyl-, 1,2,3-triformylazulenes, and 5-formylazulene derivative were also synthesized. The reaction of dimethyl 2-methylazulene-1,3-dicarboxylate with p-nitroso-N,N-dimethylaniline in the presence of NaOR (R=Me or Et) gave the corresponding 3-alkoxycarbonyl-2-[p-(dimethylamino)phenyliminomethyl]azulene-1-carboxylic acids followed by hydrolysis with hydrochloric acid to give 3-alkoxycarbonyl-2-formylazulene-1-carboxylic acids. Acetylation of 2-formylazulene-1-carboxylic acids with acetic anhydride gave five membered lactol acetates.