合成双吲哚甲烷类衍生物的研究进展

双吲哚甲烷类衍生物具有丰富的生物活性和药理活性,在医药领域得到了广泛的应用.近年来,对双吲哚甲烷类衍生物的合成研究引起了人们的热点关注.对双吲哚甲烷类衍生物的合成方法进行了综述,并将催化剂按照不同的类型分为:(1)路易斯酸催化剂,(2)分子碘催化剂,(3)质子酸催化剂,(4)固载催化剂,(5)杂多酸催化剂,(6)有机小分子催化剂,(7)配合物催化剂,(8)离子液体催化剂,(9)其它类型的催化剂.     

绿色溶剂葡萄糖酸催化合成二吲哚甲烷及其衍生物

在温和条件下,使用生物介质葡萄糖酸水溶液,简洁、绿色、高效催化合成了二吲哚甲烷及其衍生物。反应中,葡萄糖酸溶液不仅是绿色的生物反应介质而且还是催化剂,并且经过4次循环使用后,产率无明显降低。方法的优点在于葡萄糖酸溶液易得、价廉且对环境有好并可循环使用,避免了使用Brnsted或Lewis酸,减少了浪费,符合绿色化学的发展原则。     

A Meldrum's Acid Catalyzed Synthesis of Bis(indolyl)methanes in Water under Ultrasonic Condition

A highly effective Meldrum's acid catalyzed synthesis of bis(indol‐3‐yl)methanes has been developed. This reaction provides the corresponding bis(indol‐3‐yl)methanes in high yields after short reaction time in the presence of 2 mol % catalyst in water under ultrasonic condition.     

Diammonium Hydrogen Phosphate as an Efficient and Inexpensive Catalyst for the Synthesis of Bis(indolyl)methanes under Solvent-Free Conditions

Bis(indolyl)methanes were synthesized by the reaction of indole derivatives and aromatic and aliphatic aldehydes in the presence of diammonium hydrogen phosphate as a solid catalyst under solvent-free conditions. This methodology offers significant improvements for the synthesis of bis(indolyl)methanes with regard to the yield of products, simplicity in operation, and green aspects by avoiding toxic catalysts and solvents.     

Diammonium Hydrogen Phosphate as an Efficient and Inexpensive Catalyst for the Synthesis of Bis(indolyl)methanes under Solvent-Free Conditions

Summary. Bis(indolyl)methanes were synthesized by the reaction of indole derivatives and aromatic and aliphatic aldehydes in the presence of diammonium hydrogen phosphate as a solid catalyst under solvent-free conditions. This methodology offers significant improvements for the synthesis of bis(indolyl)methanes with regard to the yield of products, simplicity in operation, and green aspects by avoiding toxic catalysts and solvents.     

CuBr2‐Catalyzed Synthesis of Bis(indolyl)methanes

Abstract

Copper(II) bromide is found to be an efficient catalyst for the electrophilic substitution reaction of indole with aldehydes to afford the corresponding bis(indolyl)methanes in good yields.     

First Synthesis of Bis(di(indolyl)aryl)methanes From Bis(salicylaldehydes)

In this article, a simple method for the synthesis of bis(di(indolyl)aryl)methanes is described. The iodine‐catalyzed (5 mol %) reaction of indoles with various bis(salicylaldehyde) derivatives affords the bis(di(indolyl)aryl)methanes in excellent yields. The reaction works well under mild reaction condition with shorter reaction time.     

Hexamethylenetetraamine-Bromine Catalyzed Rapid and Efficient Synthesis of Bis(indolyl)methanes

Summary. Highly rapid and convenient syntheses of bis(indolyl)methanes in excellent yields were carried out using the inexpensive and easily available catalyst, hexamethylenetetraamine-bromine (HMTAB). Mild reaction conditions, short reaction times, and excellent yields are important features of this method.     

双吲哚烷基类化合物在无催化剂和无溶剂条件下的高效合成

在不加催化剂和溶剂条件下,由取代吲哚和取代苯甲醛合成15个已知的双吲哚烷基化合物,反应无溶剂污染,反应条件温和,收率为65%~91%。讨论了反应速度和取代基的关系,探讨了缩合反应的机理。并用1H NMR、13C NMR、IR和HRMS等技术手段确定了产物结构。     

Highly Efficient Synthesis of Bis（indolyl）methanes Catalyzed by Sodium Tetrafluoroborate

Sodium tetrafluoroborate （NaBF4） was found to catalyze the electrophilic substitution reactions of indoles with aldehydes and ketones under solvent-free conditions to afford the corresponding bis（indolyl）methanes in high yields.     

Micron Particles of AlN/Al: Efficient,Novel, and Reusable Heterogeneous Catalyst for the Synthesis of Bis(indolyl)methanes

The present work introduces for the first time the catalytic utility of micron particulate aluminium nitride (AlN/Al) as a novel and reusable heterogeneous catalyst for the synthesis of bis(indolyl)methanes involving the electrophilic substitution of indoles on aldehydes. The catalyst is recyclable and works without any significant change in its catalytic activity.     

对甲苯磺酸催化三吲哚烷基化合物的合成

室温下,吲哚与3-吲哚甲醛在对甲苯磺酸的催化下高收率得到三吲哚烷基化合物,所有产物的结构经1H NMR,IR和HR-MS表征。     

Antimony Trichloride Catalyzed Condensation of Indole and Carbonyl Compounds: Synthesis of Bis(indolyl)methanes

A mild and efficient condensation reaction of indoles with various aldehydes and ketones under catalysis of antimony trichloride (SbCl₃) afforded biologically important bis(indolyl)methanes in good yield. The structures of all the newly synthesized compounds were elucidated on the basis of IR, ¹H NMR and mass spectral data.     

Synthesis and Catalytic Application of Bimetallic and Trimetallic Magnetic Nanoalloys for the Preparation of Bis(indolyl)methanes

Russian Journal of Organic Chemistry - Some bimetallic and trimetallic magnetic nanoalloys based on cobalt, copper, and silver have been synthesized and used as and green catalysts for the...     

有机磷酸催化合成双吲哚烷烃衍生物

以联萘二酚衍生的有机磷酸为催化剂,催化吲哚和羰基化合物的亲电取代反应,合成了一系列双吲哚衍生物,收率64%～95%,其结构经1H NMR,13C NMR和HR-MS确证。     

Efficient Synthesis of Bis(heterocyclyl)methanes

The reaction of pyrrole/furan aldehyde with Grignard reagent and pyrrole/N-methyl pyrrole in sequence allows efficient synthesis of a number of meso-elaborated bis(heterocyclyl)methanes, which are otherwise difficult to obtain through a direct aldehyde condensation route.      

Utilization of flow chemistry in catalysis: New avenues for the selective synthesis of Bis(indolyl)methanes

Flow chemistry enables the preparation of bis(indolyl)methanes from various indoles and structurally divergent aldehydes using Sc(OTf)₃ catalysis. The reaction is regioselective for C-3 functionalization of the indoles, occurring over short reaction times allowing for rapid investigation of scope with straightforward work up facilitating product isolation.     

Synthesis,antibacterial and anti-inflammatory activity of bis(indolyl)methanes

A series of bioactive bis(indolyl)methanes are synthesized by one-pot green reaction of indole with various substituted aldehydes by microwave irradiation under solvent free conditions. The antibacterial activity against Staphylococcus aureus and anti-inflammatory activity of the synthesized bis(indolyl)-methanes are evaluated in vitro and compared to standard drugs tetracycline and diclofenac, respectively. The majority of the compounds showed good antibacterial and anti-inflammatory activity. Interestingly, compounds 3j, 3i, 3k and 3g exhibited much higher anti-inflammatory activity than the standard diclofenac drug and thus qualify for clinical trials to be used as an anti-inflammatory compound.     

Silica-Supported LiHSO4 as a Highly Efficient,Mild, Heterogeneous,and Reusable Catalytic System for the Solvent-Free Synthesis of Bis(indolyl)methanes

Silica-supported LiHSO₄ (LiHSO₄/SiO₂) is used as a green, cheap, and efficient catalytic system for the synthesis of bis(indolyl)methanes via the condensation of indoles with carbonyl compounds under solvent-free conditions. The reactions proceed rapidly at room temperature, and the title compounds are obtained in high to excellent yields.     

Synthesis of Pharmacologically Active Bis(indolyl) and Tris(indolyl) Derivatives Using Chlorotrimethylsilane

Chlorotrimethylsilane is found to be a comparatively fast and efficient catalyst for carrying out electrophilic substitution reactions of indoles with various aldehydes/ketones/triethylorthoformate, yielding excellent amount of bis(indolyl)methanes/tris(indolyl)methanes. The merits of this protocol are avoidance of any external energy source, minimal reaction time, simple and easy procedure and high yield under solvent free room temperature condition. The versatility of this method has been tested with various aldehydes/ketones and received satisfactory results.