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苯并三唑的光化学:1,3-双自由基的产生及分子间环加成反应——通往吲哚和二氢吡咯并[3,4-b]吲哚的新途径

Photochemistry of benzotriazoles: generation of 1,3-diradicals and intermolecular cycloaddition as a new route toward indoles and dihydropyrrolo[3,4-b]indoles.

作者信息

Al-Jalal Nader A, Ibrahim Maher R, Al-Awadi Nouria A, Elnagdi Mohamed H, Ibrahim Yehia A

机构信息

Department of Chemistry, Faculty of Science, Kuwait University, P.O. Box 5969, Safat 13060, Kuwait.

出版信息

Molecules. 2014 Dec 11;19(12):20695-708. doi: 10.3390/molecules191220695.

DOI:10.3390/molecules191220695
PMID:25514217
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6271786/
Abstract

Irradiation of benzotriazoles 1a-e at λ = 254 nm in acetonitrile solution generated the corresponding 1,3-diradicals which underwent intermolecular cycloaddition with maleimides to afford the corresponding dihydropyrrolo[3,4-b]indoles and with acetylene derivatives to afford indoles as the major products. This offers an interesting and simple access to such ring systems of potential synthetic and biological interest. The structures of the photoproducts were established spectroscopically and by single crystal X-ray crystallography.

摘要

在乙腈溶液中,将苯并三唑1a - e在λ = 254 nm下进行辐照,生成相应的1,3 - 双自由基,其与马来酰亚胺发生分子间环加成反应,得到相应的二氢吡咯并[3,4 - b]吲哚,与乙炔衍生物反应则以吲哚作为主要产物。这为获得具有潜在合成和生物学意义的此类环系提供了一种有趣且简便的方法。通过光谱学和单晶X射线晶体学确定了光产物的结构。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/298a/6271786/812e1fb0ae15/molecules-19-20695-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/298a/6271786/808217d47197/molecules-19-20695-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/298a/6271786/c6c38755a398/molecules-19-20695-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/298a/6271786/bc84139266e6/molecules-19-20695-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/298a/6271786/da296c07d978/molecules-19-20695-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/298a/6271786/764bd368b2e7/molecules-19-20695-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/298a/6271786/812e1fb0ae15/molecules-19-20695-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/298a/6271786/808217d47197/molecules-19-20695-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/298a/6271786/c6c38755a398/molecules-19-20695-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/298a/6271786/bc84139266e6/molecules-19-20695-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/298a/6271786/da296c07d978/molecules-19-20695-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/298a/6271786/764bd368b2e7/molecules-19-20695-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/298a/6271786/812e1fb0ae15/molecules-19-20695-g006.jpg

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