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Unexpected Result in the Catalytic Solvent-free Multicomponent Synthesis of 2-Amino-3-cyano-4H-chromene
Organic Preparations and Procedures International ( IF 1.2 ) Pub Date : 2019-02-15 , DOI: 10.1080/00304948.2018.1549903
Valeria Palermo 1 , Alexis A. Sosa 1 , Toa S. Rivera 1 , Luis R. Pizzio 1 , Gustavo P. Romanelli 1
Affiliation  

Multicomponent reactions (MCRs) are efficient and effective methods for the sustainable and diversity-oriented synthesis of heterocycles. In a green chemistry context, the traditional methods of performing chemical synthesis are unsustainable, and MCRs provide an important solution since they are more efficient, cost-effective, and less wasteful. A known MCR for example is the condensation between aldehyde, malononitrile, and phenol or naphthol to give 2-amino-3-cyano-4H-chromenes. In this regard, heteropolyacids and derivatives represent one of the most important categories of solid catalysts. They are widely utilized due to their acid and redox properties and represent an important family of materials used under heterogeneous and solvent-free conditions for the synthesis of different heterocycles. Keggin, WellsDawson and Preyssler heteropolyacid composites are used in heterocyclic synthesis as catalysts in several MCRs for the preparation of dihydropyrimidinones, quinazolinones, pyridines, xanthenones, imidazoles, pyrazoles, and 1,4-dihydropyridines. Recently, some applications related to the use of zirconia/heteropolyacid composites in green organic synthesis and relevant technological procedures have been reported. These include veratrole benzoylation, oleochemistry transesterification and esterification reactions, biomass valorization through the esterification of 2-furoic acid with alcohols, synthesis of bioadditives for biofuels from glycerol esterification with acetic acid, and synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes and quinoxalines. Moreover, in the last decade, great attention has been paid to 2-amino-3-cyano-4Hchromenes due to their antimicrobial, antifungal, antioxidant, and pro-apoptotic activities. The classical method for their synthesis involves the MCR among aldehydes, malononitrile, and phenol or naphthol in the presence of a catalyst, such as NaOH, Na2CO3, 21 Al2O3, 22 methanesulfonic acid, or heteropolyacid. As well, 14-aryl-14H-dibenzo[a,j]xanthenes have attractive biological properties such as antiviral, anti-inflammatory, antibacterial, and antimicrobial activity, among

中文翻译:

2-氨基-3-氰基-4H-色烯催化无溶剂多组分合成中的意外结果

多组分反应 (MCR) 是可持续和面向多样性的杂环合成的有效方法。在绿色化学背景下,进行化学合成的传统方法是不可持续的,而 MCR 提供了一种重要的解决方案,因为它们更高效、更具成本效益且浪费更少。例如,已知的 MCR 是醛、丙二腈和苯酚或萘酚之间的缩合反应,得到 2-氨基-3-氰基-4H-色烯。在这方面,杂多酸和衍生物代表了最重要的固体催化剂类别之一。由于它们的酸和氧化还原特性,它们被广泛使用,并且代表了在非均相和无溶剂条件下用于合成不同杂环的重要材料家族。凯金,WellsDawson 和 Preyssler 杂多酸复合物在杂环合成中用作多种 MCR 的催化剂,用于制备二氢嘧啶酮、喹唑啉酮、吡啶、呫吨酮、咪唑、吡唑和 1,4-二氢吡啶。最近,报道了一些与氧化锆/杂多酸复合材料在绿色有机合成中的应用和相关技术程序。这些包括藜芦苯甲酰化、油脂化学酯交换和酯化反应、通过 2-呋喃酸与醇的酯化使生物质增值、甘油与乙酸酯化合成生物燃料的生物添加剂,以及 14-芳基-14H-二苯并[a,j ]呫吨和喹喔啉。此外,在过去的十年中,2-amino-3-cyano-4Hchromenes 由于其抗菌、抗真菌、抗氧化和促凋亡活性而备受关注。其合成的经典方法包括在催化剂(例如 NaOH、Na2CO3、21 Al2O3、22 甲磺酸或杂多酸)存在下,在醛、丙二腈和苯酚或萘酚之间进行 MCR。同样,14-芳基-14H-二苯并[a,j]呫吨具有吸引人的生物学特性,例如抗病毒、抗炎、抗菌和抗微生物活性,其中
更新日期:2019-02-15
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