摘要
背景:铋盐介导的反应由于其低毒性(无毒性)和路易斯酸性能而成为合成各种药用显着化合物的有力工具。事实上,硝酸铋的LD50低于食盐。另一方面,微波诱导的化学合成被认为是现代化学中的主要绿色途径。 方法:对139篇出版物(包括一些真实的网页链接)进行了综述,主要讨论了铋盐诱导的亲电芳香取代,羰基化合物的保护 - 脱保护化学,烯胺化,氧化,碳水化合物化学,水解,加成消除途径,Paal-Knorr反应,Clauson-kaas合成,Michael加成,aza-Michael加成,Hantzsch反应,Biginelli反应,Ferrier重排,Pechmann缩合,Diels-Alder和aza-Diels-Alder反应,以及微波辐射广泛的化学转化。 结果:铋盐介导的反应被开发用于合成具有医学意义的多种有机分子。用铋盐进行的反应是环境友好的,经济的,快速的和高收率的。微波辐射已经显着加速了这些反应。据信在反应过程中铋盐在介质中释放相应的酸。然而,在NMR研究中也观察到铋盐与电负性原子的配位。与碱金属相比,铋对阴离子(例如卤化物,硝酸盐,硫酸盐和三氟甲磺酸盐)的控制(吸引力小得多)少得多。因此,它更容易与负电原子形成弱键,并有助于显着的反应。通过铋盐介导的反应获得的许多产物对于合成生物活性分子(包括抗真菌剂,抗寄生虫剂,抗癌剂和抗菌剂)以及预防利什曼病和南美锥虫病的药剂而言具有药物活性或中间产物。 结论:铋盐能够(i)在反应介质中产生无机酸,(ii)与电负性原子配位以促进反应。当试剂和催化剂(铋盐)经受微波照射时,微波通过反应容器的(玻璃)壁并且仅加热反应物,避免容器壁处的局部过热。因此,副反应和随后的副产物形成的可能性突然降低,这又增加了所需产物的收率。作为铋盐和微波辐射的协同效应,可以合理地将产品的极高的产率极高的速度合理化。
关键词: 铋盐,生物活性,催化作用,绿色合成,杂环化合物,微波照射,药物等。
Current Medicinal Chemistry
Title:Microwave-induced Bismuth Salts-mediated Synthesis of Molecules of Medicinal Interests
Volume: 24 Issue: 41
关键词: 铋盐,生物活性,催化作用,绿色合成,杂环化合物,微波照射,药物等。
摘要: Background: Bismuth salts-mediated reactions have become a powerful tool for the synthesis of diverse medicinally-significant compounds because of their low-toxicity (non-toxic) and Lewis acidic capacity. In fact, LD50 of bismuth nitrate is lower than table salt. On the other hand, microwave-induced chemical synthesis is considered as a major greener route in modern chemistry.
Methods: A total of 139 publications (including a few authentic web links) have been reviewed mainly to discuss bismuth salts-induced electrophilic aromatic substitution, protection-deprotection chemistry of carbonyl compounds, enamination, oxidation, carbohydrate chemistry, hydrolysis, addition-elimination route, Paal-Knorr reaction, Clauson-kaas synthesis, Michael addition, aza-Michael addition, Hantzsch reaction, Biginelli reaction, Ferrier rearrangement, Pechmann condensation, Diels-Alder and aza-Diels- Alder reactions, as well as effects of microwave irradiation in a wide range of chemical transformations.
Results: Bismuth salts-mediated reactions are developed for the synthesis of diverse organic molecules of medicinal significance. Reactions conducted with bismuth salts are environmentally benign, economical, rapid and high yielding. Microwave irradiation has accelerated these reactions significantly. It is believed that bismuth salts released corresponding acids in the media during the reaction. However, a coordination of bismuth salt to the electronegative atom is also observed in the NMR study. Bismuth has much less control (less attractive forces) over anions (for example, halides, nitrate, sulfate and triflates) compared to alkali metals. Therefore, it forms weak bond with electronegative atoms more readily and facilitates the reactions significantly. Many products obtained via bismuth salts-mediated reactions are medicinally active or intermediate for the synthesis of biologically active molecules including antifungal, anti-parasitic, anticancer and antibacterial agents, as well as agents to prevent Leishmaniosis and Chagas' diseases.
Conclusion: Bismuth salts are able to (i) generate mineral acids in the reaction media and (ii) coordinate with electronegative atoms to facilitate the reaction. When the reagents and the catalyst (bismuth salt) are subjected to microwave irradiation, microwave passes through the (glass) walls of the reaction vessel and heat only the reactants avoiding local overheating at the wall of the vessel. Accordingly, the possibility of side reaction and subsequent by-product formation are reduced abruptly which in turn increases the yield of the desired product. The extreme rapidity with excellent yield of the product can be rationalized as a synergistic effect of the bismuth salts and microwave irradiation.
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Cite this article as:
Microwave-induced Bismuth Salts-mediated Synthesis of Molecules of Medicinal Interests, Current Medicinal Chemistry 2017; 24 (41) . https://dx.doi.org/10.2174/0929867324666170320121142
DOI https://dx.doi.org/10.2174/0929867324666170320121142 |
Print ISSN 0929-8673 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-533X |
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