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首页> 外文期刊>Chemistry of heterocyclic compounds >Unusual Reaction of 1-Acetyl-5-bromo-1H-indole-2,3-dione with Ethyl (Triphenylphosphoranylidene)acetate
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Unusual Reaction of 1-Acetyl-5-bromo-1H-indole-2,3-dione with Ethyl (Triphenylphosphoranylidene)acetate

机译:1-乙酰基-5-溴-1H-吲哚-2,3-二酮与(三苯基膦亚基)乙酸乙酯的反常反应

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摘要

Isatins readily react with methylene triphenylphosphoranes to fonn 3-methylene-l,3-dihydro-2H-indol-2-ones, which are of practical importance [1-5]. As a result of reaction of l-acetyl-5-bromo-lH-indole-2,3-dione with the ethyl ester of triphenylphosphoranylidene acetic acid (ethoxycarbonylmethylene triphenyl-phosphorane), in addition to the usual Wittig reaction product (the yellow ethyl ester of (2Z)-(2-oxo-l,2-dihydro-3H-indol-3-ylidene)acetic acid (1)), we unexpectedly isolated a colorless "dimer": the diethyl ester of 2,1'-diacetyl-5,5'-dibromo-l,2'-dioxo-l,r,2,2',7,8,8a-heptahydrospiro{benzo[cfir|indole-6,3'-indole}-7,8-dicarboxylic acid (2).
机译:靛红很容易与亚甲基三苯基膦反应生成3-亚甲基-1,3-二氢-2H-吲哚-2-酮,这在实际中具有重要意义[1-5]。除了通常的维蒂希反应产物(黄色乙基)外,1-乙酰基-5-溴-1H-吲哚-2,3-二酮与三苯基膦亚基乙酸(乙氧基羰基亚甲基三苯基膦)的乙酯反应的结果(2Z)-(2-氧代-1,2-二氢-3H-吲哚-3-亚烷基)乙酸(1)的酯),我们意外地分离出了无色的“二聚体”:2,1'-二乙酰基5,5'-二溴-1,2'-二氧代-1,r,2,2',7,8,8a-七水螺{苯并[cfir |吲哚-6,3'-吲哚} -7,8 -二羧酸(2)。

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