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Green Synthesis of Poly‐Substituted Pyrano[4,3‐b]quinoline‐1,9‐(5H)‐dione Derivatives Using Solid Acid as Catalyst in Water
ChemistrySelect ( IF 2.1 ) Pub Date : 2020-03-25 , DOI: 10.1002/slct.201904552
Ning Yang 1 , Danmin Zhang 1 , Jianguo Zhou 1 , Chenze Qi 1 , Chunmei Li 1 , Furen Zhang 1
Affiliation  

A series of new pyrano[4,3‐b]quinoline‐1,9(5H)‐dione derivatives were synthesized via one‐pot three‐component reaction using 6‐methyl‐4‐(arylamino)‐2H‐pyran‐2‐ones, aldehydes, and 1,3‐cyclohexanediones as substrates. The application of 4‐methylbenzenesulfonyl chloride activated the hydroxyl group of pyranone and avoided the forming of ring opening product. The reaction proceeds smoothly and gives biological and pharmacological active substituted pyrano[4,3‐b]quinoline‐1,9(5H)‐dione derivatives with good to excellent yields under green conditions. A plausible mechanism for the domino process is proposed.

中文翻译:

固体酸在水中催化合成多取代的吡喃并[4,3-b]喹啉-1,9-(5H)-二酮衍生物

使用6-甲基-4-(芳基氨基)-2- H-吡喃经一锅三组分反应合成了一系列新的吡喃并[4,3 - b ]喹啉-1,9(5 H)-二酮衍生物。以2-one,醛和1,3-环己二酮为底物。4-甲基苯磺酰氯的应用激活了吡喃酮的羟基,避免了开环产物的形成。反应平稳进行,并在绿色条件下以良好或优异的收率得到具有生物学和药理活性的取代吡喃并[4,3 - b ]喹啉-1,9(5 H)-二酮衍生物。提出了一种可行的多米诺骨牌机制。
更新日期:2020-03-26
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