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3-(呋喃-2-基)-1,3-二(杂芳基)丙-1-酮通过氧化呋喃去芳构化/2-烯-1,4,7-三酮环化转化为丙-2-烯-1-酮。

Transformation of 3-(Furan-2-yl)-1,3-di(het)arylpropan-1-ones to Prop-2-en-1-ones via Oxidative Furan Dearomatization/2-Ene-1,4,7-triones Cyclization.

机构信息

Department of Chemistry, Perm State University, Bukireva st. 15, 614990 Perm, Russia.

N.D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences, Leninsky pr. 47, 119334 Moscow, Russia.

出版信息

Molecules. 2021 Apr 30;26(9):2637. doi: 10.3390/molecules26092637.

DOI:10.3390/molecules26092637
PMID:33946475
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8124928/
Abstract

The approach to 3-(furan-2-yl)-1,3-di(het)arylprop-2-en-1-ones based on the oxidative dearomatization of 3-(furan-2-yl)-1,3-di(het)arylpropan-1-ones followed by an unusual cyclization of the formed di(het)aryl-substituted 2-ene-1,4,7-triones has been developed. The cyclization step is related to the Paal-Knorr synthesis, but the furan ring formation is accompanied in this case by a formal shift of the double bond through the formation of a fully conjugated 4,7-hydroxy-2,4,6-trien-1-one system or its surrogate.

摘要

基于 3-(呋喃-2-基)-1,3-二(杂芳基)丙-2-烯-1-酮的氧化去芳构化，然后对形成的二(杂芳基)取代的 2-烯-1,4,7-三酮进行不寻常的环化，开发了 3-(呋喃-2-基)-1,3-二(杂芳基)丙-2-烯-1-酮的方法。环化步骤与 Paal-Knorr 合成有关，但在这种情况下，呋喃环的形成伴随着双键的正式迁移，通过形成完全共轭的 4,7-羟基-2,4,6-三烯-1-酮系统或其替代物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/07df/8124928/45504922c71e/molecules-26-02637-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/07df/8124928/b82f54f63a29/molecules-26-02637-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/07df/8124928/da49b721aee8/molecules-26-02637-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/07df/8124928/b8a8fa9ec896/molecules-26-02637-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/07df/8124928/dcd148141eb1/molecules-26-02637-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/07df/8124928/45504922c71e/molecules-26-02637-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/07df/8124928/b82f54f63a29/molecules-26-02637-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/07df/8124928/da49b721aee8/molecules-26-02637-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/07df/8124928/b8a8fa9ec896/molecules-26-02637-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/07df/8124928/dcd148141eb1/molecules-26-02637-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/07df/8124928/45504922c71e/molecules-26-02637-sch004.jpg

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