Transition-metal-free [3 + 3] annulation of indol-2-ylmethyl carbanions to nitroarenes. A novel synthesis of indolo[3,2-b]quinolines (quindolines)
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.
| Main Authors: | , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2018-01-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.14.14 |
| _version_ | 1818874128945381376 |
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| author | Michał Nowacki Krzysztof Wojciechowski |
| author_facet | Michał Nowacki Krzysztof Wojciechowski |
| author_sort | Michał Nowacki |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-19T13:05:41Z |
| format | Article |
| id | doaj.art-80e1a66322374e649d5c2b54f28f6a14 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-19T13:05:41Z |
| publishDate | 2018-01-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-80e1a66322374e649d5c2b54f28f6a142022-12-21T20:20:04ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972018-01-0114119420210.3762/bjoc.14.141860-5397-14-14Transition-metal-free [3 + 3] annulation of indol-2-ylmethyl carbanions to nitroarenes. A novel synthesis of indolo[3,2-b]quinolines (quindolines)Michał Nowacki0Krzysztof Wojciechowski1Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, PolandInstitute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, PolandIndol-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.https://doi.org/10.3762/bjoc.14.14carbanionscyclizationheterocyclesnitroarenesnucleophilic substitutionsilylation |
| spellingShingle | Michał Nowacki Krzysztof Wojciechowski Transition-metal-free [3 + 3] annulation of indol-2-ylmethyl carbanions to nitroarenes. A novel synthesis of indolo[3,2-b]quinolines (quindolines) Beilstein Journal of Organic Chemistry carbanions cyclization heterocycles nitroarenes nucleophilic substitution silylation |
| title | Transition-metal-free [3 + 3] annulation of indol-2-ylmethyl carbanions to nitroarenes. A novel synthesis of indolo[3,2-b]quinolines (quindolines) |
| title_full | Transition-metal-free [3 + 3] annulation of indol-2-ylmethyl carbanions to nitroarenes. A novel synthesis of indolo[3,2-b]quinolines (quindolines) |
| title_fullStr | Transition-metal-free [3 + 3] annulation of indol-2-ylmethyl carbanions to nitroarenes. A novel synthesis of indolo[3,2-b]quinolines (quindolines) |
| title_full_unstemmed | Transition-metal-free [3 + 3] annulation of indol-2-ylmethyl carbanions to nitroarenes. A novel synthesis of indolo[3,2-b]quinolines (quindolines) |
| title_short | Transition-metal-free [3 + 3] annulation of indol-2-ylmethyl carbanions to nitroarenes. A novel synthesis of indolo[3,2-b]quinolines (quindolines) |
| title_sort | transition metal free 3 3 annulation of indol 2 ylmethyl carbanions to nitroarenes a novel synthesis of indolo 3 2 b quinolines quindolines |
| topic | carbanions cyclization heterocycles nitroarenes nucleophilic substitution silylation |
| url | https://doi.org/10.3762/bjoc.14.14 |
| work_keys_str_mv | AT michałnowacki transitionmetalfree33annulationofindol2ylmethylcarbanionstonitroarenesanovelsynthesisofindolo32bquinolinesquindolines AT krzysztofwojciechowski transitionmetalfree33annulationofindol2ylmethylcarbanionstonitroarenesanovelsynthesisofindolo32bquinolinesquindolines |