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