A new organocatalyst for Friedel-Crafts alkylation of 2-naphthols with isatins: application of an organo-click strategy for the cascade synthesis of highly functionalized molecules

The three-component Friedel-Crafts alkylation/Huisgen cycloaddition (FCA/HC) reactions of 2-naphthols, substituted isatins and azides under dimethylamino-ethanol/Cu^I-catalysis furnished highly functionalized 1,4-disubstituted [1,2,3]-triazoles.     

Intramolecular Cyclization of 4-Isocyanato-3-(2-naphthyl)-1-phenylpyrazole Under Friedel-Crafts Reaction Conditions

4-Isocyanato-3-(2-naphthyl)-1-phenylpyrazole cyclized under the influence of AlCl₃ to give 2H-benzo[h]pyrazolo[4,3-c]isoquinoline.     

Syntheses of 1-Azaazulan-2-One Analogs of Adrenergic Agents

The Friedel-Crafts reaction of 1-azaazulan-2-ones with α-haloacid chloride in the presence of aluminum trichloride gives the corresponding α-haloacyl derivatives. Treatment of these reaction products first with various secondary amines and then with sodium borohydride gives new adrenergic active amine derivatives.     

Intramolecular alkene Friedel-Crafts cyclization of 1-allyl-1-N-(ortho-alkylphenylamino)cyclohexanes. A useful route to alkyl substituted dihydrospiro[(1H)quinoline-2,1-cyclohexanes]. Unprecedented ipso-substitution of alkyl groups

An unprecedented intramolecular Friedel-Crafts ipso-alkylation at the ortho-alkyl group of the N-arylamino moiety of 1-allyl-1-N-arylaminocycloalkanes to give alkyl substituted dihydrospiro[(1H) quinoline-2,1^′-cycloalkanes] is reported. Unexpected results were explained in the context of intramolecular ipso-substitution of alkyl groups and their 1,2-rearrangement. A plausible mechanism for this type of Friedel-Crafts alkylation by an alkene moiety promoted by a Brönsted acid (H₂SO₄) is proposed.     

On the mechanism of conversion of 4-carboxy-3,4-dihydro-3-phenyl-1(2H)-isoquinolones to indeno[1,2-c]isoquinolines by thionyl chloride

It has been known for a long time that thionyl chloride can effectively mediate the transformation of 4-carboxy-3,4-dihydro-3-phenyl-1(2H)-isoquinolones to indeno[1,2-c]isoquinolines. The mechanism of this unique transformation, however, remains to be established. Evidence is presented to demonstrate that (1) the two-electron dehydrogenation precedes Friedel-Crafts cyclization and (2) the two-electron dehydrogenation occurs via H-4 deprotonation and subsequent O-sulfinylation of the lactam moiety instead of C-sulfinylation of the carbon α to the carboxyl group.     

Investigating direct routes to an advanced intermediate for the synthesis of C-20 diterpene alkaloids

Rapid access to the ABCE ring system of the C-20 diterpene alkaloids was achieved by silver (I) promoted intramolecular Friedel-Crafts arylation of a functional group specific 5-bromo-3-azabicyclo[3.3.1]nonane derivative.     

Recyclable hafnium(IV) bis(perfluorooctanesulfonyl)amide complex for catalytic Friedel-Crafts acylation and Prins reaction in fluorous biphase system

In fluorous biphase system, hafnium(IV) bis(perfluorooctanesulfonyl)amide complex (Hf[N(SO₂C₈F₁₇)₂]₄) was found to be a highly reactive and recyclable Lewis acid catalyst for Friedel-Crafts acylation and Prins reaction at significantly low catalyst loadings (≤1 mol%). In these reactions, Hf[N(SO₂C₈F₁₇)₂]₄ is selectively soluble in the lower fluorous phase and can be recovered simply by phase separation. Furthermore, the catalyst can be reused without decrease of activity.     

2-(4′-氨基苯甲酰基)苯甲酸的合成方法改进

以邻苯二甲酸酐,乙酰苯胺为原料,二氯乙烷为溶剂,无水三氯化铝为催化剂,通过Friedel-Crafts酰基化反应制得2-(4′-乙酰氨基苯甲酰基)苯甲酸(1),1在酸性条件下回流,除去乙酰基得到2-(4′-氨基苯甲酰基)苯甲酸(2)。通过1H NMR,IR,MS和元素分析对1和2的结构进行了表征。最佳的Friedel-Crafts反应条件为:邻苯二甲酸酐20 mmol,n(邻苯二甲酸酐)∶n(乙酰苯胺)=1∶1,n(邻苯二甲酸酐)∶n(AlCl3)=1∶3,于45℃反应2 h,收率70.4%。     

卟啉基超交联聚合物的合成及其对二氧化碳和汞(Ⅱ)离子的吸附北大核心CSCD

超交联聚合物(HCPs)具有较高的比表面积和独特的孔结构,且制备方法简单、合成原料广泛,是多孔有机聚合物的研究热点之一。卟啉是一类由4个吡咯类亚基的α-碳原子通过次甲基桥互联形成的大分子杂环化合物,可与多种金属形成稳定的配合物,在重金属的吸附与检测、气体的吸附与分离等方面具有很好的应用。卟啉结构的HCPs也有了较多的报道,然而当前报道的卟啉结构HCPs几乎均是通过Friedel-Crafts烷基化反应构筑的。Friedel-Crafts酰基化反应在卟啉结构HCPs上报道较少。而通过Friedel-Crafts酰基化反应制备的聚合物表面含大量羰基,为其进一步功能化提供了可能。但是,这类聚合物的比表面积低、孔结构差,而其优良孔结构的构建是亟待解决的问题。为此,本文在四苯基卟啉与1,2,4,5-苯四甲酸酐通过Friedel-Crafts酰基化反应制备的聚合物的基础上,进一步通过席夫碱反应,用含刚性三嗪环的三聚氰胺将其进一步交联,合成了三聚氰胺修饰的卟啉基超交联聚合物。结果发现,三聚氰胺的引入不仅实现了超交联聚合物孔结构的支撑,使得聚合物比表面积极大增长(从2 m^(2)/g增加到118 m^(2)/g),且具有优良的多级孔结构。三聚氰胺修饰卟啉基超交联聚合物的高氮质量分数(46.28%)和多级孔结构使其对CO_(2)(93 mg/g,273 K,101 kPa)和Hg^(2+)(494.1 mg/g,298 K)具有较好的吸附。     

氯磷灰石负载金属卤化物催化芳香化合物的Friedel-Crafts 苄基化反应研究

以氯磷灰石为载体,采用水热法制各了氯磷灰石负载金属卤化物固体酸催化剂,通过IR,XRD对载体和催化剂的结构进行了表征.研究了催化剂对芳香化合物与苄基氯、苄基溴和苄基醇的Friedel-Crafts烷基化反应.结果表明,溴化锌负载氯磷灰石催化剂的活性最高,而且催化剂易回收和重复使用,催化剂重复使用5次活性没有明显降低.