Cascade Reaction of 1,1-Enediamines with 2-Benzylidene-1H-indene-1,3(2H)-diones: Selective Synthesis of Indenodihydropyridine and Indenopyridine Compounds.,ACS Omega

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Cascade Reaction of 1,1-Enediamines with 2-Benzylidene-1H-indene-1,3(2H)-diones: Selective Synthesis of Indenodihydropyridine and Indenopyridine Compounds.
ACS Omega ( IF 3.7 ) Pub Date : 2019-04-11 , DOI: 10.1021/acsomega.9b00407
Qin Luo ₁ , Rong Huang ₁ , Qiang Xiao ₁ , Ling-Bin Kong ₁ , Jun Lin ₁ , Sheng-Jiao Yan ₁

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A concise and environmentally friendly route for the synthesis of diverse indenodihydropyridines (3) via a cascade reaction of 1,1-eneamines (1) with benzylidene-1H-indene-1,3(2H)-diones (BIDs) (2) in ethanol media was developed. The targeted compounds were efficiently obtained by only filtration without any further post-treatment. In the one-step cascade reaction, C-C and C-N bonds were constructed. In addition, when 1,4-dioxane was used as a solvent and the mixture of 1,1-eneamines (1) was refluxed with benzylidene-1H-indene-1,3(2H)-diones (BIDs) (2) for about 12 h, indenopyridine compounds (4) were produced. Two kinds of indenopyridine derivatives 3-4 resulted from alternative solvents and temperatures. The reaction had the following features: mild temperature, atom economy, high yields, and potential biological activity of the product.

中文翻译：

1,1-烯二胺与2-苄基-1H-茚-1,3（2H）-二酮的级联反应：茚并二氢吡啶和茚并吡啶化合物的选择性合成。

通过1,1-烯胺（1）与亚苄基-1H-茚-1,3（2H）-二酮（BID）（2）的级联反应合成各种茚并二氢吡啶（3）的简捷环保方法开发了乙醇培养基。仅通过过滤就可以有效地获得目标化合物，而无需任何进一步的后处理。在一步式级联反应中，构建了CC和CN键。此外，当使用1,4-二恶烷作为溶剂，并将1,1-烯胺（1）的混合物与亚苄基-1H-茚-1,3（2H）-二酮（BID）（2）回流时，大约12小时，产生茚并吡啶化合物（4）。两种茚并吡啶衍生物3-4是由不同的溶剂和温度引起的。该反应具有以下特征：温和的温度，原子经济性，高产率和产物的潜在生物活性。

更新日期：2019-04-11

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