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Chemo‐ and diastereoselective synthesis of new oxa[3.3.3]propellane via a domino cascade four‐component reaction based on diketene
Journal of Heterocyclic Chemistry ( IF 2.4 ) Pub Date : 2020-08-14 , DOI: 10.1002/jhet.4126
Atieh Rezvanian 1 , Mehri Salimi 1 , Vahideh Zadsirjan 1 , Fahame Mahmoodi 1 , Majid M. Heravi 1
Affiliation  

A highly convergent, eco‐friendly and straightforward synthesis of new O‐fused heterocycles, functionalized indeno[1,2‐b]furan derivatives was successfully accomplished through a one‐pot four‐component cascade reaction involving, ninhydrin, malononitrile, diketene and various primary amines in the presence of a catalytic quantity of triethylamine in ethanol at ambient temperature, in one pot fashion. This new efficient cascade reaction generates two rings by the simultaneous construction of C‐N (one), C‐O (two) and C‐C (two) multiple bonds, presumably through a sequence of Knoevenagel reaction/Michael addition/intramolecular O‐cyclization and imine‐enamine/keto‐enol tautomerization. The merits of this protocol are highlighted as utilization of inexpensive commercially accessible starting materials, operational simplicity, atom economy, clean reaction profile, simple work‐up procedure being conducted at ambient temperature in relatively short reaction times, preventing chromatographic purification, giving excellent yields, and tolerance to a wide variety of functional groups.

中文翻译:

基于双烯酮的多米诺级联四组分反应化学合成和非对映选择性合成新的氧杂[3.3.3]丙炔

通过一锅四组分级联反应,包括茚三酮,丙二腈,双烯酮和各种化合物,成功地完成了高度融合,生态友好,直接合成新的O稠合杂环,官能化茚并[1,2- b ]呋喃衍生物的工作。在室温下,在乙醇中催化量的三乙胺存在下,以一锅法制备伯胺。这种新的有效级联反应通过同时构造C‐N(一个),C‐O(两个)和C‐C(两个)多个键而生成两个环,大概是通过一系列的Knoevenagel反应/ Michael加成/分子内O环化和亚胺-烯胺/酮-烯醇互变异构。该协议的优点突出:利用廉价的可商购的起始原料,操作简便,原子经济,清洁的反应谱,在环境温度下以相对较短的反应时间进行简单的后处理程序,防止色谱纯化,获得优异的收率,以及对各种功能组的容忍度。
更新日期:2020-08-14
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