Lithium-Promoted Cycloaddition of Indole-2,3-dienolates and Carbon Disulfide as a One-Pot Route to Thiopyrano[4,3‑b]indole-3(5H)‑thiones
A new approach for the annulation of a thiopyrane ring to an indole core under mild conditions was developed. Treating 2-methyl-3-acylindoles with lithium diisopropyl amide leads to the elimination of a proton from the 2-methyl group. The lithium indole-2,3-dienolates obtained were found to react wi...
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| Veröffentlicht in: | Journal of organic chemistry 2021-09, Vol.86 (17), p.11698-11707 |
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| container_end_page | 11707 |
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| container_issue | 17 |
| container_start_page | 11698 |
| container_title | Journal of organic chemistry |
| container_volume | 86 |
| creator | Suzdalev, Konstantin F Vyalyh, Julia V Tkachev, Valery V Lysenko, Ekaterina A Burov, Oleg N Lisovin, Anton V Kletskii, Mikhail E Kurbatov, Sergey V |
| description | A new approach for the annulation of a thiopyrane ring to an indole core under mild conditions was developed. Treating 2-methyl-3-acylindoles with lithium diisopropyl amide leads to the elimination of a proton from the 2-methyl group. The lithium indole-2,3-dienolates obtained were found to react with CS2 to give the corresponding thiopyrano[4,3-b]indole-3(5H)-thiones. The mechanism represents a stepwise addition through ion-pair formation, according to PCM/B3LYP/6-311++G**, PBE1PBE/6-311++G**, and MP2//HF/6-311++G** quantum chemical calculations. AIM calculations revealed the essential role of the Li atom at all stages of the process. |
| doi_str_mv | 10.1021/acs.joc.1c01200 |
| format | Article |
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Treating 2-methyl-3-acylindoles with lithium diisopropyl amide leads to the elimination of a proton from the 2-methyl group. The lithium indole-2,3-dienolates obtained were found to react with CS2 to give the corresponding thiopyrano[4,3-b]indole-3(5H)-thiones. The mechanism represents a stepwise addition through ion-pair formation, according to PCM/B3LYP/6-311++G**, PBE1PBE/6-311++G**, and MP2//HF/6-311++G** quantum chemical calculations. 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Org. Chem</addtitle><date>2021-09-03</date><risdate>2021</risdate><volume>86</volume><issue>17</issue><spage>11698</spage><epage>11707</epage><pages>11698-11707</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>A new approach for the annulation of a thiopyrane ring to an indole core under mild conditions was developed. Treating 2-methyl-3-acylindoles with lithium diisopropyl amide leads to the elimination of a proton from the 2-methyl group. The lithium indole-2,3-dienolates obtained were found to react with CS2 to give the corresponding thiopyrano[4,3-b]indole-3(5H)-thiones. The mechanism represents a stepwise addition through ion-pair formation, according to PCM/B3LYP/6-311++G**, PBE1PBE/6-311++G**, and MP2//HF/6-311++G** quantum chemical calculations. 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| title | Lithium-Promoted Cycloaddition of Indole-2,3-dienolates and Carbon Disulfide as a One-Pot Route to Thiopyrano[4,3‑b]indole-3(5H)‑thiones |
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