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纳米晶且可重复使用的 ZnO 催化剂用于在水相中通过一锅法三组分反应组装稠合多功能化 4H-色烯:更绿色的“NOSE”方法。

Nanocrystalline and reusable ZnO catalyst for the assembly of densely functionalized 4H-chromenes in aqueous medium via one-pot three component reactions: a greener "NOSE" approach.

机构信息

Department of Chemistry, University of Calcutta, Kolkata-700009, India.

出版信息

J Org Chem. 2013 Jun 21;78(12):6170-81. doi: 10.1021/jo400763z. Epub 2013 Jun 6.

DOI:10.1021/jo400763z
PMID:23701231
Abstract

An ecofriendly, one-pot, three component ZnO nanoparticles-mediated synthesis of 4H-chromene in water under thermal condition has been described. The highly product-selective three component electrophilic reaction of 2-hydroxybenzaldehyde with an active methylene compound and another carbon-based varied nature of nucleophile has been developed by a reversible alkylation procedure using greener "NOSE" approach. Greenness of the process was well instituted, as water was used both as reaction media as well as medium for the synthesis of catalyst. In these reactions, the use of nano-ZnO as a catalyst was documented to be crucial for rendering the reactions possible in water media, while replacing nano-ZnO with other acids or bases resulted in the generation of too many side products. The catalyst can be efficiently recycled up to the sixth run, an essential point in the area of green chemistry. The methodology provides cleaner conversion, shorter reaction times, and high selectivity, which make the protocol globally putative. The crystal structures of 4H-chromene, easily produced by a chromatography-free highly product-selective reaction, were explored by means of single crystal X-ray diffraction analysis, and H-bonding arrangements of one signified compound prepared is presented. In optimized mild conditions, the isolated yields are 86-93%.

摘要

已描述了在热条件下在水中通过环保的一锅法、三组分 ZnO 纳米粒子介导合成 4H-色烯。通过使用更环保的“NOSE”方法的可逆烷基化程序,开发了具有高产物选择性的三组分亲电反应,其中 2-羟基苯甲醛与活性亚甲基化合物和另一种基于碳的各种亲核试剂反应。该过程的绿色性得到了很好的建立,因为水既用作反应介质,也用作催化剂的合成介质。在这些反应中,使用纳米 ZnO 作为催化剂对于在水介质中进行反应至关重要,而用其他酸或碱代替纳米 ZnO 会导致产生太多的副产物。催化剂可在第六次运行时有效地回收,这在绿色化学领域是一个重要的方面。该方法提供了更清洁的转化、更短的反应时间和更高的选择性,这使得该方案在全球范围内具有潜力。通过无色谱的高产物选择性反应很容易制备 4H-色烯的晶体结构,通过单晶 X 射线衍射分析进行了探索,并呈现了一种有意义的化合物的氢键排列。在优化的温和条件下,分离产率为 86-93%。

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