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可见光促进[3+2]环加成反应高效合成萘并[2,3-f]呋喃-4,9-二酮

An Efficient Synthesis of Naphtho[2,3-]furan-4,9-diones via Visible-Light-Mediated [3+2] Cycloaddition Reaction.

机构信息

National & Local Joint Engineering Research Center of Targeted and Innovative Therapeutics, Chongqing Engineering Laboratory of Targeted and Innovative Therapeutics, Chongqing Key Laboratory of Kinase Modulators as Innovative Medicine, Chongqing Collaborative Innovation Center of Targeted and Innovative Therapeutics, College of Pharmacy & IATTI, Chongqing University of Arts and Sciences, Chongqing 402160, China.

Key Laboratory of Biorheological Science and Technology, Ministry of Education, College of Bioengineering, Chongqing University, Chongqing 400030, China.

出版信息

Molecules. 2023 Jun 13;28(12):4751. doi: 10.3390/molecules28124751.

DOI:10.3390/molecules28124751
PMID:37375306
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10301255/
Abstract

Naphtho[2,3-]furan-4,9-dione is an important privileged structural motif which is present in natural products, drugs, and drug candidates. Herein, visible-light-mediated [3+2] cycloaddition reaction for the synthesis of naphtho[2,3-]furan-4,9-diones and dihydronaphtho[2,3-]furan-4,9-diones has been developed. Under environmentally friendly conditions, a variety of title compounds were delivered in good yields. This new protocol shows excellent regioselectivity and remarkable functional group tolerance. This approach provides a powerful, green, efficient, and facile means to expand the structural diversity of naphtho[2,3-]furan-4,9-diones and dihydronaph-tho[2,3-]furan-4,9-diones as promising scaffolds for novel drug discovery.

摘要

萘并[2,3-f]呋喃-4,9-二酮是一种重要的特权结构基序，存在于天然产物、药物和药物候选物中。本文开发了一种可见光介导的[3+2]环加成反应，用于合成萘并[2,3-f]呋喃-4,9-二酮和二氢萘并[2,3-f]呋喃-4,9-二酮。在环保条件下，以良好的收率得到了多种标题化合物。该新方法具有优异的区域选择性和显著的官能团耐受性。该方法为扩展萘并[2,3-f]呋喃-4,9-二酮和二氢萘并[2,3-f]呋喃-4,9-二酮的结构多样性提供了一种强大、绿色、高效、简便的方法，作为新型药物发现的有前途的支架。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0893/10301255/ec458dc870e4/molecules-28-04751-sch007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0893/10301255/ec6614595d9d/molecules-28-04751-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0893/10301255/b1047f7fd705/molecules-28-04751-sch006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0893/10301255/ec458dc870e4/molecules-28-04751-sch007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0893/10301255/ec6614595d9d/molecules-28-04751-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0893/10301255/b1047f7fd705/molecules-28-04751-sch006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0893/10301255/ec458dc870e4/molecules-28-04751-sch007.jpg

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