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1,7-二炔的光诱导自由基串联环化反应：一种用于功能化喹啉-2(1H)-酮发散组装的方法。

Photoinduced radical tandem annulation of 1,7-diynes: an approach for divergent assembly of functionalized quinolin-2(1H)-ones.

作者信息

Chen Daixiang, Song Zhi-Jie, Yan Shenghu, Li Guigen, Wang Jia-Yin, Zhang Yue

机构信息

School of Pharmacy, Changzhou University, Changzhou, Jiangsu, China.

Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX, United States.

出版信息

Front Chem. 2024 Mar 26;12:1371978. doi: 10.3389/fchem.2024.1371978. eCollection 2024.

DOI:10.3389/fchem.2024.1371978
PMID:38595704
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11002210/
Abstract

The first photocatalytic trichloromethyl radical-triggered annulative reactions of amide-linked 1,7-diynes with polyhalomethanes were established for the flexible assembly of functionalized quinolin-2(1H)-ones with generally acceptable yields. With the installation of the aryl group (R) into the alkynyl moiety, -center radical-initiated Kharasch-type addition/nucleophilic substitution/elimination cascade to produce quinolin-2(1H)-ones-incorporating -dihaloalkene, whereas three examples of polyhalogenated quinolin-2(1H)-ones were afforded when amide-linked 1,7-diynes bearing two terminal alkyne units were subjected to BrCX by exploiting dry acetonitrile as a solvent.

摘要

首次建立了酰胺连接的1,7-二炔与多卤代甲烷的光催化三氯甲基自由基引发的环化反应，用于灵活组装功能化喹啉-2(1H)-酮，产率普遍可接受。通过将芳基(R)引入炔基部分，中心自由基引发的Kharasch型加成/亲核取代/消除级联反应生成含有二卤代烯烃的喹啉-2(1H)-酮，而当以干燥乙腈为溶剂，使带有两个末端炔基单元的酰胺连接的1,7-二炔与BrCX反应时，得到了三个多卤代喹啉-2(1H)-酮的例子。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/645f/11002210/e5e8d405c698/FCHEM_fchem-2024-1371978_wc_sch6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/645f/11002210/4b2b99dfaba7/fchem-12-1371978-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/645f/11002210/49baf8564269/FCHEM_fchem-2024-1371978_wc_sch1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/645f/11002210/4aa3af2c939c/FCHEM_fchem-2024-1371978_wc_sch2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/645f/11002210/35f5b68c4a9e/FCHEM_fchem-2024-1371978_wc_sch3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/645f/11002210/bc2d7d308a78/FCHEM_fchem-2024-1371978_wc_sch4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/645f/11002210/a92a60d78d00/FCHEM_fchem-2024-1371978_wc_sch5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/645f/11002210/9543c0e5ab7c/fchem-12-1371978-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/645f/11002210/e5e8d405c698/FCHEM_fchem-2024-1371978_wc_sch6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/645f/11002210/4b2b99dfaba7/fchem-12-1371978-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/645f/11002210/49baf8564269/FCHEM_fchem-2024-1371978_wc_sch1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/645f/11002210/4aa3af2c939c/FCHEM_fchem-2024-1371978_wc_sch2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/645f/11002210/35f5b68c4a9e/FCHEM_fchem-2024-1371978_wc_sch3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/645f/11002210/bc2d7d308a78/FCHEM_fchem-2024-1371978_wc_sch4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/645f/11002210/a92a60d78d00/FCHEM_fchem-2024-1371978_wc_sch5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/645f/11002210/9543c0e5ab7c/fchem-12-1371978-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/645f/11002210/e5e8d405c698/FCHEM_fchem-2024-1371978_wc_sch6.jpg

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