苯并咪唑类化合物催化合成的研究进展

苯并咪唑类化合物在医药、农药等方面具有广泛的应用,因此这类化合物合成的新方法备受关注.从合成苯并咪唑类化合物的不同的原料出发,综述了近年来催化合成苯并咪唑化合物的研究新进展.     

苯并咪唑类化合物的合成研究进展

苯并咪唑类化合物应用广泛. 按不同的合成原料和合成方法进行分类, 综述了近年来苯并咪唑类化合物合成研究的新进展.     

基于氨基酸的苯并咪唑合成研究进展

苯并咪唑类化合物在药物化学、生物化学、配位化学以及催化、分子识别、阻燃等领域具有重要应用.氨基酸类化合物是一类来源广泛的功能性合成子,因此近年来基于氨基酸的苯并咪唑合成与功能改性研究受到人们的广泛关注.综述了以各种天然与非天然氨基酸为原料,以溶液法、微波法、固相法等合成技术合成与改性苯并咪唑的新进展.     

水相中可见光催化腈合成苯并咪唑衍生物

报道了在水相中可见光下1,2-苯二胺与苯腈的环化反应,合成了一系列苯并咪唑类化合物.反应用便宜、易处理、对环境无污染的曙红Y作为光催化剂.室温下在水相中反应,获得的产物有较好收率,最高产率可达到91%.提供了一种合成苯并咪唑类化合物的简便经济的方法.     

铜催化串联C-H官能化反应构建苯并咪唑稠合二氢苯并唑类化合物

苯并咪唑稠合二氢苯并唑是一类复杂的氮氧杂环,在生物医药和功能性材料中具有较高的应用价值.本文在空气氛围中以苯并咪唑和2-溴苯酚为原料、廉价Cu(Ⅱ)为催化剂,采用"一锅法"合成了苯并咪唑稠合二氢苯并唑类化合物,反应经历了N-芳基化、sp~2 C-H活化、C-O环化的串联过程.研究表明,该反应对于苯并咪唑类衍生物,以及其他反应底物(如2-碘苯酚和2-羟基苯硼酸)均具有一定的官能团耐受性.本文为高效合成苯并咪唑稠合二氢苯并唑类化合物提供了一种简便方法.     

N-取代苯基-N’-（2-苯并咪唑甲酰基）脲的合成及抑菌活性

许多芳酰基脲类化合物具有良好的杀虫活性,有些还具有一定的杀菌、除草、植物生长调节等生物活性,已成为农药研究和开发的热点。迄今为止,已研制出除虫脲、氟铃脲、灭幼脲、伏虫隆、苏脲1号等20多种商品化的苯甲酰脲类杀虫剂。另一方面,苯并咪唑类化合物,如多菌灵、氰菌灵、麦穗宁等是一类活性很强的内吸性杀菌剂;但是,随着使用时间的延长,病害菌的抗性也越来越强,导致该类杀菌剂活性降低,甚至在一些地区丧失了杀菌能力。因此,研究新型苯并咪唑类杀菌剂具有很大的应用价值。为了寻找具有高效杀菌活性的新型苯并咪唑类化合物,本文利用活性结构拼接原理,将2-苯并咪唑基引入芳酰基脲类化合物的分子中,     

苯并咪唑基荧光化学传感器的合成与应用研究进展

苯并咪唑类化合物在多种有机溶剂和水溶液中能够发出特征荧光,而且在一定条件下荧光性质会因多种因素而发生改变,因此其在荧光检测领域的应用受到了广泛的关注.综述了苯并咪唑类传感器的合成及其在各种金属离子、阴离子、无机物小分子、金属氧化物纳米粒子和有机小分子等物质检测中应用的新进展,并展望了苯并咪唑基荧光化学传感器的发展趋势.     

取代甲基亚磺酰基苯并咪唑类化合物的合成

合成了一系列取代甲基硫代苯并咪唑类化合物，并在过氧乙酸的氧化下得到了 取代甲基亚磺酰基苯并咪唑类化合物，收率较好(79%～97%)，代替了用间氯过氧苯 甲酸进行氧化，反应过程稳定，降低了成本。     

微波辅助技术在苯并咪唑合成中的应用

苯并咪唑类化合物作为一种重要的N-杂有机化合物,在药物化学、材料化学、合成化学等领域显示出广阔的应用前景。传统方法合成苯并咪唑具有速度缓慢、效率低下等缺点。微波辅助合成苯并咪唑由于速度快、反应时间短、收率高、易纯化以及环境友好等优点越来越受到人们的关注。本文介绍了近年来微波辅助合成苯并咪唑的研究与应用。     

N-(酰基二茂铁)苯并咪唑类化合物的合成和表征

将二茂铁磺酰氯或二茂铁甲酰氯和1H-苯并咪唑衍生物反应,合成了12个未见文献报道的N-(酰基二茂铁)苯并咪唑类化合物,用IR、1HNMR、元素分析和MS对其结构进行了表征。结果表明,含有活泼氢的苯并咪唑衍生物能与二茂铁酰氯生成相应的N-(酰基二茂铁)苯并咪唑衍生物,并有较好的收率。     

苯并咪唑及其衍生物合成与应用研究进展

苯并咪唑及其衍生物具有良好的生物活性, 而且是一种重要的药物中间体. 由于它们具有良好的生物活性和反应活性, 一直都是研究的热点. 从该类化合物的合成与应用两个方面综述了近年来该领域的重要研究成果.     

Rapid and Cheap Synthesis of Benzimidazoles via Intermittent Microwave Promotion: A Simple and Potential Industrial Application of Air as Oxidant

Using inexpensive KI as the catalyst in the presence of ambient air, benzimidazoles were synthesized from aromatic aldehydes and o-phenylenediamine with excellent yields via intermittent microwave irradiation without reflux equipment. The synthesis process was mild and only needed only a short reaction time (7–10 min). As a simple example of the utilization of molecular oxygen under mild conditions, this method provides a novel way to synthesize benzimidazoles. The industrial synthesis of benzimidazoles may be realized by a cycle of microwave irradiation.     

Microwave‐Assisted Solid‐Phase Synthesis of a 1,2‐Disubstituted Benzimidazole Library by Using a Phosphonium Linker

An efficient and rapid microwave‐assisted solid‐phase method for the synthesis of 5‐methyl‐1,2‐disubstituted benzimidazoles derivatives has been developed. The phosphonium linker, obtained by reaction between polymer‐supported triphenylphosphine and 4‐fluoro‐3‐nitrobenzyl iodide, underwent aromatic substitution with primary amines, followed by one‐pot reaction with aldehydes in the presence of SnCl₂·2H₂O, yielded the benzimidazole system under microwave irradiation. The final products were released from the resin with NaOH under microwave irradiation and were obtained in high purity and good overall yield.     

Rapid microwave-assisted liquid-phase combinatorial synthesis of 2-(arylamino)benzimidazoles

An efficient, facile, and practical liquid-phase combinatorial synthesis of benzimidazoles under microwave irradiation is described. In the first step of reaction sequence, polymer-bound activated aryl fluoride was condensed with selective primary amines via an ipso-fluoro displacement reaction. Reduction of the polymer-bound nitro group followed by cyclization with isothiocyanates afforded immobilized benzimidazoles. The desired products were obtained in high yield with high purity after detaching from the soluble matrix. All reactions involved (S(N)Ar reaction, reduction, cyclization, and support cleavage) were performed completely within a few minutes under microwave irradiation. The coupling of microwave technology with liquid-phase combinatorial synthesis constitutes a novel and particularly attractive avenue for the rapid generation of structurally diverse libraries.     

Microwave-assisted one step high-throughput synthesis of benzimidazoles

One-pot synthesis of benzimidazoles from diamines and carboxylic acids was developed under microwave irradiation condition, which provided a practical and efficient method for high-throughput synthesis of this important class of heterocyclic compounds.     

Combinatorial synthesis of biheterocyclic benzimidazoles by microwave irradiation

Liquid phasel synthesis of biheterocyclic benzimidazoles by controlled microwave irradiation was investigated. Polymer immobilized o-phenylenediamines was synthesized under microwave irradiation. The resulting PEG bound diamines was N-acylated with 4-fluoro-3-nitrobenzoic acid selectively in primary aromatic amino moiety. Nucleophilic aromatic substitution of amide was performed with various amines then cyclized to form the first benzimidazole scaffold in acidic condition. Successive reduction, cyclization with isothiocyanates yielded 5-(benzimidazol-2-yl)benzimidazoles. The desired products were released from the polymer support to afford the tri-substituted bis-benzimidazoles in good yields and purity.     

A Rapid and Convenient Synthesis of Derivatives of Imidazoles under Microwave Irradiation

An efficient and a quick microwave‐assisted synthesis of benzimidazoles and trisubstituted imidazoles was developed. Three benzimidazoles were obtained as a result of the condensation of 1,2‐phenylenediamine with carboxylic acids and acetoacetic ester without catalyst. A series of trisubstituted imidazoles were synthesized by condensation of benzil, aromatic aldehyde and ammonium acetate in the presence of glacial acetic acid.     

Imidazolium chloride-catalyzed synthesis of benzimidazoles and 2-substituted benzimidazoles from o-phenylenediamines and DMF derivatives

A facile, general, and economical synthesis of diversely functionalized benzimidazoles and 2-substituted benzimidazoles has been realized via the imidazolium chloride-catalyzed cyclization of o-phenylenediamines with DMF derivatives. This protocol shows a broad substrate scope for aliphatic, aromatic, and heteroaromatic amides. A series of benzimidazoles and 2-substituted benzimidazoles have been obtained in moderate to excellent yields.     

CN bond formation and cyclization: A straightforward and metal-free synthesis of N-1-alkyl-2-unsubstituted benzimidazoles

A straightforward and metal-free synthesis of N-1-alkyl-2-unsubstituted benzimidazoles from the corresponding o-fluoro aryl formamidines and primary amines using microwave irradiation is described. The displacement of -F by the primary amine and cyclization to form the corresponding benzimidazoles took place in one pot.     

Cp2ZrCl2-catalyzed synthesis of 2-aminovinyl benzimidazoles under microwave conditions

A microwave-assisted general method for the synthesis of 2-aminovinyl benzimidazoles has been developed.Treatment of the 1,2-phenylenediamines and N-arylated/N,N-dialkylated 3-aminoacroleins with bis(cyclopentadienyl)zirconium(IV) dichloride(Cp2Zr Cl2) as the catalyst under microwave irradiation for 3–5 min followed by in situ Mn O2 oxidation afforded thirteen 2-aminovinyl benzimidazoles in good yields.