SYNTHESIS OF E AND Z 1-AMINO-2-ARYL(ALKYL)-CYCLOPROPANECARBOXYLIC ACIDS VIA MELDRUM DERIVATIVES
SYNTHESIS OF E AND Z 1-AMINO-2-ARYL(ALKYL)-CYCLOPROPANECARBOXYLIC ACIDS VIA MELDRUM DERIVATIVES
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DOI：
10.1016/s0040-4020(01)83489-x
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发表时间：
1985-01-01
期刊：
影响因子：
2.1
通讯作者：
ALVAREZ, EF
中科院分区：
文献类型：
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作者：
IZQUIERDO, ML;ARENAL, I;ALVAREZ, EF
5-芳基烯（烷基烯）-2,2-二甲基-1,3-二恶烷-4,6-二酮(1)（Meldrum的酸衍生物）与甲基二甲基亚砜反应得到1-芳基（烷基）-6,6-二甲基-4,8-二氧基-5,7-二氧基[2.5]辛烷(2)，在甲氧基钠或氢氧化铵的作用下，分别只得到e- 1-甲氧基-羰基-2-芳基-环丙烷羧酸(4)或z -1-氨基酰基-2-芳基（烷基）-环丙烷羧酸(7)。化合物4在curtius型反应条件下得到z -甲基1-异氰酸酯-2-芳基-环丙烷羧酸酯(5)，而衍生物7用次溴酸盐处理得到e- 1-甲氧基-羰基氨基-2-芳基（烷基）-环丙烷羧酸酯(8)。化合物5和8与盐酸反应生成相应的Z和e -1-氨基-2-芳基（烷基）-环丙烷羧酸盐酸盐(6)。通过1H-NMR谱数据分析所得化合物的立体化学性质。
The reaction of 5-arylidene(alkylidene)-2,2-dimethyl-1,3-dioxane-4,6-diones (1)(Meldrum''s acid derivatives) with dimethylsulfoxonium methylide gave 1-aryl(alkyl)-6,6-dimethyl-4,8-dioxo-5,7-dioxaspiro [2.5] octanes (2) which, on treatment with sodium methoxide or ammonium hydroxide, gave exclusively E-1-methoxy-carboyl-2-aryl-cyclopropanecarboxylic acids (4) or Z-1-carbamoyl-2-aryl(alkyl)-cyclopropanecarboxylic acids (7), respectively. Compounds, 4, under conditions of Curtius-type reactions, yielded Z-methyl 1-isocyanate-2-aryl-cyclopropanecarboxylates (5), while derivatives 7 were treated with hypobromite, leading to E-1-methoxy-carbonylamino-2-aryl(alkyl)-cyclopropanecarboxylic acids (8). Reaction of compounds 5 and 8 with hydrochloric acid produced the corresponding Z and E-1-amino-2-aryl(alkyl)-cyclopropanecarboxylic acids hydrochlorides (6). The 1H-NMR spectral data were analyzed to deduce the stereochemistry of the compounds obtained.