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Application of [PVP-SO3H] HSO4 as an Efficient Polymeric-Based Solid Acid Catalyst in the Synthesis of Some Benzimidazole Derivatives
Organic Preparations and Procedures International ( IF 1.5 ) Pub Date : 2020-07-03 , DOI: 10.1080/00304948.2020.1765654
Fatemeh Pakpour Roudsari 1 , Mohadeseh Seddighi 1 , Farhad Shirini 1 , Hassan Tajik 1
Affiliation  

Benzimidazoles, benzoxazoles and benzothiazoles are essential types of heterocyclic compounds that are plentiful in nature. They have a wide spectrum of pharmacological and biological activities such as anti-viral, anti-inflammatory, anti-hypertensive, antimicrobial and antihistamine properties. Benzimidazoles display unique properties as DNA minor-groove binding agents as well as ligands to transition metals. Clearly this is an important structural element which can be found in many commercial medicines (Fig. 1). In general, there are two methods for the synthesis of benzimidazoles. The first method involves the treatment of o-aminobenzenethiol, o-phenylenediamine and o-aminophenol with carboxylic acids or their derivatives such as nitriles, imidates, or orthoesters using a strong acidic catalyst. The second method, which leads to 2phenyl-1H-benzo[d]imidazoles, involves the two-step reaction of o-phenylenediamines with aldehydes in the presence of appropriate reagents. Although it is known that these reactions are accelerated with different catalysts, many of them occur in homogeneous conditions or have such problems as using high amounts of catalyst, high costs, long reaction times, side products, severe reaction conditions or high oxidizing power. The search for inexpensive, environmentally friendly, and non-homogeneous catalysts, which can be easily separated and reused, is a major concern to heterocyclic chemists. Heterogeneous solid acid catalysts are practical constituents in numerous industrial processes. These types of catalysts have some advantages over homogeneous Br€ onsted acid catalysts. These advantages include having: easy production and separation, higher surface areas, lower costs and energy savings. Often they are non-toxic and non-corrosive, allow the reaction to be performed under under mild conditions and decrease the number of reaction steps. The presence of Br€ onsted-acid functional groups (particularly SO3H and HSO4) within the structures of solid acids, makes them useful for solvent-free conditions. [PVP-SO3H] HSO4 is a polymeric-based solid acid catalyst (Fig. 2), that has been developed in our research group and has been used in a number of significant reactions, including the synthesis of tetrahydrobenzimidazo[2,1-b]quinazolin-1(2H)-ones, 1-(benzothiazolylamino)

中文翻译:

[PVP-SO3H]HSO4作为高效高分子固体酸催化剂在苯并咪唑衍生物合成中的应用

苯并咪唑、苯并恶唑和苯并噻唑是自然界中含量丰富的杂环化合物的基本类型。它们具有广泛的药理和生物活性,例如抗病毒、抗炎、抗高血压、抗菌和抗组胺特性。苯并咪唑作为 DNA 小沟结合剂以及过渡金属的配体显示出独特的性质。显然,这是一个重要的结构元素,可以在许多商业药物中找到(图 1)。一般来说,苯并咪唑的合成有两种方法。第一种方法涉及使用强酸性催化剂用羧酸或其衍生物如腈、亚胺酯或原酸酯处理邻氨基苯硫醇、邻苯二胺和邻氨基苯酚。第二种方法,产生 2-苯基-1H-苯并[d]咪唑,涉及邻苯二胺与醛在适当试剂存在下的两步反应。虽然已知这些反应可以用不同的催化剂加速,但其中许多是在均相条件下发生的,或者存在催化剂用量大、成本高、反应时间长、副产物多、反应条件苛刻或氧化能力强等问题。寻找廉价、环保、非均相且易于分离和重复使用的催化剂是杂环化学家的主要关注点。多相固体酸催化剂是许多工业过程中的实用成分。这些类型的催化剂与均相溴酸催化剂相比具有一些优势。这些优势包括:易于生产和分离、更高的表面积、更低的成本和节能。通常它们是无毒和无腐蚀性的,允许反应在温和的条件下进行并减少反应步骤的数量。固体酸结构中溴酸官能团(特别是 SO3H 和 HSO4)的存在使它们可用于无溶剂条件。[PVP-SO3H] HSO4 是一种聚合物基固体酸催化剂(图 2),由我们研究组开发并已用于许多重要反应,包括合成四氢苯并咪唑 [2,1-b ]quinazolin-1(2H)-ones, 1-(benzothiazolylamino) 使反应在温和的条件下进行,减少反应步骤的数量。固体酸结构中溴酸官能团(特别是 SO3H 和 HSO4)的存在使它们可用于无溶剂条件。[PVP-SO3H] HSO4 是一种聚合物基固体酸催化剂(图 2),由我们研究组开发并已用于许多重要反应,包括合成四氢苯并咪唑 [2,1-b ]quinazolin-1(2H)-ones, 1-(benzothiazolylamino) 使反应在温和的条件下进行,减少反应步骤的数量。固体酸结构中溴酸官能团(特别是 SO3H 和 HSO4)的存在使它们可用于无溶剂条件。[PVP-SO3H] HSO4 是一种聚合物基固体酸催化剂(图 2),由我们研究组开发并已用于许多重要反应,包括合成四氢苯并咪唑 [2,1-b ]quinazolin-1(2H)-ones, 1-(benzothiazolylamino)
更新日期:2020-07-03
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