Methyl 1-hydroxyindole-3-acetate (1a) produced novel hexacyclic 8,17-bis(methoxycarbonylmethyl)-1,10-diaza-9,20-dioxakabutane (3) as a major product by the reaction with 85% formic acid, while its reaction with trifluoroacetic acid generated exclusively another 2,2’-bisindole dimer, 1-hydroxy-3,3’-di(methoxycarbonylmethyl)-2,2’-bisindole (4). Reaction of 1a with mineral acid such as HCl afforded nucleophile substituted 5-chloroindole derivative (6). Products and their distribution changed depending on the structure of 1-hydroxyindole. Species of acid, reaction conditions, side chain structure of 1-hydroxyindole at the 3-position are additional factors for governing the product formation. In the cases that the side chain has a C—C—N structure, nucleophilic substitution reaction occurred effectively, and was applied for the preparation of N-feruloylserotonin (46d), an alkaloid isolated from safflower seed. 1-Hydroxymelatonin (69), having a methoxy group on the benzenoid part, afforded (dl)-3a,3a’-bis(pyrrolo[2,3-b]indole) compound (72) by the treatment with 85% formic acid. Products’ structures are unequivocally determined by X-ray single crystallographic analyses.

中文翻译：

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1-羟基吲哚：阿魏酸5-羟色胺，红花种子碱，新型环系统化合物，1,10-Diaza-9,20-dioxokabutanes，2,2'-双吲哚和（

1-羟基吲哚-3-乙酸甲酯（1a）与85％的甲酸反应生成了主要产物新的六环8,17-双（甲氧羰基甲基）-1,10-二氮杂-9,20-二氧杂丁烷（3），其与三氟乙酸的反应仅生成另一个2,2'-双吲哚二聚体1-羟基-3,3'-二（甲氧基羰甲基）-2,2'-双吲哚（4）。1a与无机酸例如HCl反应，得到亲核试剂取代的5-氯吲哚衍生物（6）。产物及其分布根据1-羟基吲哚的结构而变化。酸的种类，反应条件，3-羟基1-羟基吲哚的侧链结构是控制产物形成的其他因素。在侧链具有CC结构的情况下，亲核取代反应有效地发生，并被用于制备N-阿魏酰羟色胺（46d），一种从红花种子中分离出来的生物碱。通过在85％的甲酸处理下，在苯甲酸酯部分具有甲氧基的1-羟基褪黑激素（69）得到（dl ）-3a，3a′-双（吡咯并[2，3- b ]吲哚）化合物（72）。 。产品的结构是通过X射线单晶分析明确确定的。