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Ceric ammonium nitrate catalyzed one-pot three-component microwave-assisted synthesis of indole-substituted fused pyrimidine and pyridine derivatives
Tetrahedron ( IF 2.1 ) Pub Date : 2024-02-18 , DOI: 10.1016/j.tet.2024.133883
Sharmil N. Anjirwala , Saurabh K. Patel

The study investigates the synthesis of fused pyridine and pyrimidine derivatives known for their diverse biological activities and structural versatility which serve as pivotal building blocks in organic synthesis. A series of indole-substituted cyanamide derivatives were synthesized by one-pot three-component cyclo-condensation between Indole-3-carboxaldehyde, malononitrile, and electron-rich aromatic and heterocyclic amines by employing several methods such as grinding, microwave irradiation and conventional reflux in the presence of ceric ammonium nitrate and DMF. The nuclei differ concerning the heterocyclic amines such as pyridine, pyrimidine, pyrazine, thiazole, and tetrazole. The newly synthesized compounds were characterized by IR, H NMR, C NMR, and Mass spectra. The reaction proceeds via Knoevenagel condensation, Michael addition, and intramolecular cyclization. The employed methodology offers the convenient advantages of cascade one-pot condensation, easy isolation, short reaction time, and excellent yield (83–95%).

中文翻译:

硝酸高铈铵催化一锅三组分微波辅助合成吲哚取代稠合嘧啶及吡啶衍生物

该研究研究了稠合吡啶和嘧啶衍生物的合成,这些衍生物以其多样化的生物活性和结构多功能性而闻名,它们是有机合成的关键组成部分。以3-吲哚甲醛、丙二腈、富电子芳香胺和杂环胺为原料,采用研磨、微波辐射、常规回流等多种方法,通过一锅三组分环缩合反应,合成了一系列吲哚取代氰胺衍生物。在硝酸高铈铵和 DMF 存在下。杂环胺如吡啶、嘧啶、吡嗪、噻唑和四唑的核不同。新合成的化合物通过IR、H NMR、C NMR和质谱进行了表征。该反应通过诺文格尔缩合、迈克尔加成和分子内环化进行。所采用的方法具有级联一锅缩合、易于分离、反应时间短和产率优异(83-95%)的便利优势。
更新日期:2024-02-18
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