Formation of N-acetyl-2,3-dihydroindoles by the electrochemical cleavage of the carbon-chlorine bond in N-allyl-2-chloroacetanilides
Formation of N-acetyl-2,3-dihydroindoles by the electrochemical cleavage of the carbon-chlorine bond in N-allyl-2-chloroacetanilides
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DOI：
10.3891/acta.chem.scand.52-0549
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发表时间：
1998-05-01
期刊：
影响因子：
--
通讯作者：
Hammerich, O
中科院分区：
文献类型：
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作者：
Dias, M;Gibson, M;Hammerich, O
n -烷基-2-氯乙酰苯胺的电化学诱导自由基环化形成n -乙酰-2,3-二氢吲哚，其中苯基环含有一个吸电子取代基，如氰基。n -烷基-2-氯乙酰苯胺在(E)-二苯乙烯作为电子转移剂存在下成功环化，得到1-乙酰-3-甲基-213-二氢吲哚。n -肉桂基-2-氯乙酰苯胺的间接电化学还原主要导致肉桂基断裂，仅得到n -乙酰基-3-苄基-2,3-二氢吲哚的低收率。
The electrochemically induced radical cyclization of N-alkyl-2-chloroacetanilides to form N-acetyl-2,3-dihydroindoles has been demonstrated where the phenyl ring contains an electron withdrawing substituent such as cyano. Cyclization of N-alkyl-2-chloroacetanilide was successful in the presence of (E)-stilbene as electron transfer agent yielding 1-acetyl-3-methyl-213-dihydroindole. Indirect electrochemical reduction of N-cinnamyl-2-chloroacetanilide leads mainly to cleavage of the cinnamyl group and only a low yield of N-acetyl-3-benzyl-2,3-dihydroindole was obtained.