An operationally simple and time-efficient approach has been developed for the synthesis of racemic N-substituted 3-(2-aryl-2-oxoethyl)-3-hydroxyindolin-2-ones by a piperidine-catalysed aldol reaction between aryl methyl ketones and N-alkylisatins. These aldol products were used successfully as strategic intermediates for the preparation of N-substituted (E)-3-(2-hetaryl-2-oxoethylidene)indolin-2-ones by a stereoselective dehydration reaction under acidic conditions. The products have all been fully characterized by 1H and 13C NMR spectroscopy, by mass spectrometry and, for a representative selection, by crystal structure analysis. In each of (RS)-1-benzyl-3-hydroxy-3-[2-(4-methoxyphenyl)-2-oxoethyl]indolin-2-one, C24H21NO4, (Ic), and (RS)-1-benzyl-3-{2-[4-(dimethylamino)phenyl]-2-oxoethyl}-3-hydroxyindolin-2-one, C25H24N2O3, (Id), inversion-related pairs of molecules are linked by O-H...O hydrogen bonds to form R22(10) rings, which are further linked into chains of rings by a combination of C-H...O and C-H...π(arene) hydrogen bonds in (Ic) and by C-H...π(arene) hydrogen bonds in (Id). The molecules of (RS)-1-benzyl-3-hydroxy-3-[2-oxo-2-(pyridin-4-yl)ethyl]indolin-2-one, C22H18N2O3, (Ie), are linked into a three-dimensional framework structure by a combination of O-H...N, C-H...O and C-H...π(arene) hydrogen bonds. (RS)-3-[2-(Benzo[d][1,3]dioxol-5-yl)-2-oxoethyl]-1-benzyl-3-hydroxyindolin-2-one, C24H19NO5, (If), crystallizes with Z' = 2 in the space group P-1 and the molecules are linked into complex sheets by a combination of O-H...O, C-H...O and C-H...π(arene) hydrogen bonds. In each of (E)-1-benzyl-3-[2-(4-fluorophenyl)-2-oxoethylidene]indolin-2-one, C23H16FNO2, (IIa), and (E)-1-benzyl-3-[2-oxo-2-(thiophen-2-yl)ethylidene]indolin-2-one, C21H15NO2S, (IIg), the molecules are linked into simple chains by a single C-H...O hydrogen bond, while those of (E)-1-benzyl-3-[2-oxo-2-(pyridin-4-yl)ethylidene]indolin-2-one, C22H16N2O2, (IIe), are linked by three C-H...O hydrogen bonds to form sheets which are further linked into a three-dimensional structure by C-H...π(arene) hydrogen bonds. There are no hydrogen bonds in the structures of either (E)-1-benzyl-3-[2-(4-methoxyphenyl)-2-oxoethylidene]indolin-2-one, C24H19NO3, (IIc), or (E)-1-benzyl-5-chloro-3-[2-(4-chlorophenyl)-2-oxoethylidene]indolin-2-one, C23H15Cl2NO2, (IIh), but the molecules of (IIh) are linked into chains of π-stacked dimers by a combination of C-Cl...π(arene) and aromatic π-π stacking interactions.

中文翻译：

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N-取代的3-(2-芳基-2-氧代乙基)-3-羟基二氢吲哚-2-酮的合成及其转化为N-取代的(E)-3-(2-芳基-2-氧代亚乙基)二氢吲哚-2-其中：四种 3-羟基化合物和五种氧亚乙基产物的合成序列、光谱表征和结构。

开发了一种操作简单且省时的方法，通过芳基甲基酮和芳基甲基酮之间的哌啶催化羟醛反应合成外消旋 N-取代 3-(2-芳基-2-氧代乙基)-3-羟基二氢吲哚-2-酮。 N-烷基靛红。这些羟醛产物成功地用作通过酸性条件下的立体选择性脱水反应制备N-取代的(E)-3-(2-杂芳基-2-氧代亚乙基)二氢吲哚-2-酮的战略中间体。所有产品均已通过 1H 和 13C NMR 光谱、质谱分析以及晶体结构分析（对于代表性选择）进行了充分表征。在(RS)-1-苄基-3-羟基-3-[2-(4-甲氧基苯基)-2-氧代乙基]二氢吲哚-2-酮、C 24 H 21 NO 4 、(Ic)和(RS)-1-苄基中的每一个中-3-{2-[4-(二甲基氨基)苯基]-2-氧代乙基}-3-羟基吲哚啉-2-酮，C25H24N2O3，(Id)，反转相关的分子对通过OH...O氢键连接形成R22(10)环，其通过(Ic)中的CH...O和CH...π(芳烃)氢键的组合以及CH...π(芳烃)进一步连接成环链(Id)中的氢键。(RS)-1-苄基-3-羟基-3-[2-氧代-2-(吡啶-4-基)乙基]二氢吲哚-2-酮分子，C22H18N2O3，(Ie)，连接成三个由 OH...N、CH...O 和 CH...π(芳烃) 氢键组合而成的三维骨架结构。(RS)-3-[2-(苯并[d][1,3]二氧杂环戊烯-5-基)-2-氧代乙基]-1-苄基-3-羟基二氢吲哚-2-酮，C24H19NO5，(If)，结晶空间群 P-1 中 Z' = 2，分子通过 OH...O、CH...O 和 CH...π(芳烃) 氢键连接成复合片。在(E)-1-苄基-3-[2-(4-氟苯基)-2-氧亚乙基]二氢吲哚-2-酮、C23H16FNO2、(IIa)和(E)-1-苄基-3-[ 2-氧代-2-(噻吩-2-基)亚乙基]吲哚啉-2-酮，C21H15NO2S，(IIg)，分子通过单个 CH...O 氢键连接成简单的链，而 (E )-1-benzyl-3-[2-oxo-2-(pyridin-4-yl)ethylidene]indolin-2-one, C22H16N2O2, (IIe) 通过三个 CH...O 氢键连接形成片材它们通过CH...π(芳烃)氢键进一步连接成三维结构。(E)-1-苄基-3-[2-(4-甲氧基苯基)-2-氧代亚乙基]二氢吲哚-2-酮、C24H19NO3、(IIc) 或 (E)- 结构中不存在氢键1-苄基-5-氯-3-[2-(4-氯苯基)-2-氧亚乙基]吲哚啉-2-酮，C23H15Cl2NO2，(IIh)，但(IIh)的分子连接成π堆积链通过 C-Cl...π(芳烃) 和芳香族 π-π 堆积相互作用的组合形成二聚体。