Phosphorus-containing Derivatives of Indole and Pyrrole. (Review)

Data on the synthesis and chemical properties of the phosphorus-containing derivatives of indoles and pyrroles, published in 1976-1998, are reviewed. The introduction of substituents containing tri- and tetracoordinated phosphorus atom into the heterocycle and the side chain is discussed. Information on the biological activity is presented.     

A Study on the Phosphorylation of Indole,Imidazole, Carbazole,and Phenothiazine Derivatives

Abstract

N-Heterocycles including indolecarbaldehyde, substituted benzimidazoles, and methylimidazole could be efficiently phosphorylated by diethyl chlorophosphate at room temperature in different solvents using alkali carbonate or triethylamine as the base. However, the phosphorylation of N-heterocycles with a lower reactivity at the NH function, such as carbazole and phenothiazine, could not be conducted to complete conversion under the conditions applied.     

An Efficient Ultrasound‐Assisted Synthesis of N‐Alkyl Derivatives of Carbazole,Indole, and Phenothiazine

Heterocyclic compounds bearing an acidic hydrogen atom attached to nitrogen such as carbazole, indole, and phenothiazine can be efficiently alkylated in DMSO or N,N‐DMF under ultrasonic irradiation in the presence of potassium hydroxide as a base. In almost all cases, a dramatic reduction of the reaction time results and a clear yield increase accompanied by an improved quality of the products occurs.     

新型吡咯类衍生物的合成

2,5-己二酮和胺(氨基硫脲、硫脲、苯胺、氨基酸)经过Paal-Knorr反应合成6个2,5-二甲基-N-取代吡咯衍生物;分别以新合成的N-吡咯甘氨酸、N-苯基吡咯化合物为原料,进行酯化反应和Mannich,Friedel-Craft反应,合成3个N-(2,5-二甲基吡咯)甘氨酸酯类化合物和2个N-苯基-2,5-二甲基吡咯衍生物.所有化合物都通过IR,1HNMR,13CNMR,HRMS波谱方法对其结构进行了确证.     

Spectrophotometric Determination of Diphenylamine,Pyrrole, and Indole - A Kinetic Study

Abstract

The use of p-dimethylaminocinnamaldehyde (p-DAC) has been described for the colorimetric determination of diphenylamine (DPA), Pyrrole (Py) and Indole (In) in acidic media. The kinetics of the reactions were studied and a mechanism for the reactions has been proposed. The reaction products were isolated, and identified using IR, NMR and elemental analysis.     

喹啉取代咔唑化合物的合成

以咔唑为原料,通过乙酰化反应合成了2-乙酰基咔唑(2)和3,6-二乙酰基咔唑(5);2和5分别与2-氨基二苯甲酮衍生物在酸催化下通过典型的Frledl(a)ender环化反应合成了一系列新的2-(4-取代苯基)喹啉咔唑和3,6-二(4-取代苯基)喹啉咔唑,其结构经1H NMR,IR和元素分析表征.     

N-乙基咔唑甲酰化衍生物的合成

以咔唑为原料,经烷基化和甲酰化反应合成了3-甲酰基-N-乙基咔唑和3,6-二甲酰基-N-乙基咔唑,其结构经1H NMR, IR和MS表征.重点研究了反应条件对甲酰化反应的影响.研究结果表明,甲酰化反应的较适宜条件为: 1 10 mmol, n(DMF) : n(1)=10 : 1, 1,2-二氯乙烷(25 mL)为溶剂,回流反应8 h～48 h.通过选择适当的反应条件,可以提高产率以及控制单乙酰化和双乙酰化产物的选择性.     

Alcoholysis of 2,2-Dichloropropyl Derivatives of Carbazole, Phenothiazine, and Phenoxazine

Reactions of 9-(2,2-dichlorocyclopropyl)carbazole, 10-(2,2-dichlorocyclopropyl)phenothiazine, and 10-(2,2-dichlorocyclopropyl)phenoxazine with alcohols in the system t-BuOK-DMSO yield the corresponding N-(1-alkoxy-2-propynyl) derivatives. Hydrolysis of 9-(1-methoxy-2-propynyl)carbazole and 10-(1-methoxy-2-propynyl)phenothiazine in 60% aqueous dioxane in the presence of sulfuric acid gives the corresponding heterocyclic amine and 2-propynal.     

2种吲哚衍生物的N-烷基化产物的制备

吲哚-3-乙醛酸甲酯和3-吲哚乙腈在碱存在下,以烷基卤或硫酸烷基酯为亲电试剂进行N-烷基化反应,合成了6种新的N-烷基化吲哚化合物。 研究了吲哚化合物及烷基化试剂的结构、溶剂和碱对N-烷基化反应的影响。 具有强吸电子取代基的吲哚-3-乙醛酸甲酯使用弱碱Cs2CO3在室温就可顺利进行烷基化反应,产率达到93%;而具有较弱吸电子取代基的3-吲哚乙腈,需要使用强碱NaH才能进行烷基化反应。     

Carbazole Derivatives as Potential Antimicrobial Agents

Microbial infection is a leading cause of death worldwide, resulting in around 1.2 million deaths annually. Due to this, medicinal chemists are continuously searching for new or improved alternatives to combat microbial infections. Among many nitrogen-containing heterocycles, carbazole derivatives have shown significant biological activities, of which its antimicrobial and antifungal activities are the most studied. In this review, miscellaneous carbazole derivatives and their antimicrobial activity are discussed (articles published from 1999 to 2022).     

V形咔唑衍生物的合成及荧光性质

以N-烷基咔唑作为电子给体和共轭桥中心, 二米基硼作为端基电子受体, 合成了两个V形A-π-D-π-A型新化合物: 3,6-二{[(E)-2-(5-二米基硼)噻吩]乙烯基}-N-丁基-咔唑 {N-butyl-3,6-bis{(E)-2-[5-(dimesitylboryl)thiophen-2-yl]-vinyl}-carbazole, BBTC}和3,6-二[(E)-(4-二米基硼)苯乙烯基]-N-己基-咔唑, {N-hexyl-3,6-bis[(E)-4-(dimesitylboryl)-styryl]-carbazole, BBSC}. 这两个化合物在蓝绿光波段都有较强的荧光发射. 光谱数据表明, 扩大共轭体系并在端基引入含硼基团导致吸收谱和发射谱显著红移, 并增大分子内电荷转移.     

新型手性咔唑类衍生物的合成与表征

首次用手性Hajos酮的衍生物(2)与PCl3在Fischer条件下制得手性吲哚类化合物(3和4);3和4分别成肟后进行Beckmann裂解反应,合成了两个系列的新型的咔唑类衍生物(3～9),其结构经1H NMR, 13C NMR, IR, MS和元素分析表征.9的结构经X-射线单晶衍射分析确证.     

吲哚衍生物的合成及其海洋防污性能

以吲哚和酰氯(苯甲酰氯及苯磺酰氯)为原料，合成了7个N-酰基取代吲哚类化合物(a~g)，其结构经¹H NMR和元素分析确证。研究了化合物对球等鞭金藻、亚心形扁藻和舟形藻以及藤壶幼虫的生长抑制活性。结果表明：当吲哚结构连接电负性较高的基团时，化合物对藻类和藤壶幼虫的生长抑制性较好，其中以连接苯磺酰基化合物的抑制效果最佳。目标化合物对藤壶幼虫12 h和24 h的半致死浓度(LC₅₀)明显低于底物吲哚，其中以苯磺酰基取代的化合物最低。采用目标化合物制备的海洋防污涂料，浅海挂板90 d后，对海洋污损生物的附着表现出明显的抑制作用。     

Efficient,Three-Component Synthesis of Pyrrole Derivatives Catalyzed by Iodobenzene and Oxone

A simple and highly efficient three-component method using easily available amines, nitrostyrene, and diketones in one pot has been developed for synthesis of pyrroles in the presence of catalytic amounts of iodobenzene and Oxone as oxidant. The protocol has been used to afford wide range of pyrroles in moderate to good yields.     

"一锅法"合成N-乙基咔唑乙酰化衍生物

以N-乙基咔唑为原料,通过“一锅法”合成了未见文献报道的单乙酰化衍生物3-乙酰基-9-乙基咔唑和双乙酰化衍生物3,6-二乙酰基-9-乙基咔唑,其结构经1H NMR,IR,MS和元素分析表征。     

The Glc Separation of Indole Amines and Indole Alcohols as Heptafluorobutyryl Derivatives

Abstract

Indole amines and indole alcohols were converted to heptafluoro-butyryl (HFB) derivatives by an acyl transfer reaction with heptafluoro-butyrylimidazole. The indole NH group as well as all amino and hydroxyl groups were acylated. The HFB derivatives have excellent gas chroma-tographic properties and can be used with either hydrogen flame or electron capture detection systems. Mass spectra of the HFB derivatives of biologic N, N-dialkyl indole amines are very characteristic; these compounds can be identified easily by GLC-MS methods.     

具有双光子吸收的咔唑类分子的设计、合成及光谱特性

设计、合成了四个新的咔唑类具有较大双光子吸收截面的化合物,研究它们的光谱特性,对双光子吸收的构效关系进行初步探索.