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Transition-metal-free [3 + 3] annulation of indol-2-ylmethyl carbanions to nitroarenes. A novel synthesis of indolo[3,2-b]quinolines (quindolines).

ABSTRACT: Indol-2-ylmethyl carbanions stabilized by alkoxycarbonyl, cyano or benzenesulfonyl groups react with nitroarenes to form ?H-adducts, which in the presence of base (triethylamine or DBU) and trimethylchlorosilane transform into indolo[3,2-b]quinoline derivatives in moderate to good yields.

SUBMITTER: Nowacki M

PROVIDER: S-EPMC5789443 | biostudies-literature | 2018

REPOSITORIES: biostudies-literature

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Transition-metal-free [3 + 3] annulation of indol-2-ylmethyl carbanions to nitroarenes. A novel synthesis of indolo[3,2-b]quinolines (quindolines).

Nowacki Michał M Wojciechowski Krzysztof K

Beilstein journal of organic chemistry 20180123

Indol-2-ylmethyl carbanions stabilized by alkoxycarbonyl, cyano or benzenesulfonyl groups react with nitroarenes to form σH-adducts, which in the presence of base (triethylamine or DBU) and trimethylchlorosilane transform into indolo[3,2-b]quinoline derivatives in moderate to good yields. ...[more]

PMID: 29441142

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Organometallic indolo[3,2-c]quinolines versus indolo[3,2-d]benzazepines: synthesis, structural and spectroscopic characterization, and biological efficacy.

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