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

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 (R1) into the alkynyl moiety, C-center radical-initiated Kharasch-type addition/nucleophilic substitution/elimination cascade to produce quinolin-2(1H)-ones-incorporating gem-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 BrCX3 by exploiting dry acetonitrile as a solvent.

SUBMITTER: Chen D 

PROVIDER: S-EPMC11002210 | biostudies-literature | 2024

REPOSITORIES: biostudies-literature

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

Chen Daixiang D   Song Zhi-Jie ZJ   Yan Shenghu S   Li Guigen G   Wang Jia-Yin JY   Zhang Yue Y  

Frontiers in chemistry 20240326

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<sup>1</sup>) into the alkynyl moiety, <i>C</i>-center radical-initiated Kharasch-type addition/nucleophilic substitution/elimination cascade to produce quinolin-2(1H)-ones-incorporating <i>gem</i>-dihaloalkene, wh  ...[more]

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