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An Efficient One-Pot Synthesis of Densely Functionalized Fused-Quinolines via Sequential Ugi4CC and Acid-Mediated Povarov-Type Reaction
ACS Combinatorial Science ( IF 3.903 ) Pub Date : 2017-08-08 00:00:00 , DOI: 10.1021/acscombsci.7b00095
Anirban Ghoshal 1, 2 , Doddapaneni Yugandhar 1, 2 , Jagadeesh Babu Nanubolu 3 , Ajay Kumar Srivastava 1, 2
Affiliation  

A divergent synthesis of fused-quinolines has been explored by performing Ugi four-component condensation and sulfuric acid promoted deprotection/Povarov-type reaction in one-pot. The process involves Ugi condensation of propiolic acids, aldehydes/ketones, aminoaldehyde acetals and isocyanides followed by sulfuric acid promoted deprotection and Povarov-type reaction with anilines in ethanol. This method enables straightforward access to the structurally diverse 2,3-dihydro-1H-pyrrolo[3,4-b]quinolin-1-ones (DHPQ), 3,4-dihydrobenzo[b][1,6]naphthyridin-1(2H)-ones (DHBN), and 2,3,4,5-tetrahydro-1H-azepino[4,3-b]quinolin-1-ones (THAQ), starting from readily available starting materials.

中文翻译:

通过顺序的Ugi4CC和酸介导的Povarov型反应有效地一锅合成密集功能化的熔融喹啉

通过在一锅中进行Ugi四组分缩合和硫酸促进的脱保护/ Povarov型反应,探索了稠合喹啉的多样化合成方法。该过程涉及丙酸,醛/酮,氨基醛缩醛和异氰酸酯的Ugi缩合,然后由硫酸促进的脱保护作用以及在乙醇中与苯胺的Povarov型反应。此方法可直接访问结构多样的2,3-二氢-1 H-吡咯并[3,4- b ]喹啉-1-酮(DHPQ),3,4-二氢苯并[ b ] [1,6]萘啶- 1(2 H)-ones(DHBN)和2,3,4,5-tetrahydro-1 H -azepino [4,3 - b ] quinolin-1-ones(THAQ),从容易获得的起始原料开始。
更新日期:2017-08-08
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