Sequential N-Arylation and Intramolecular Imine Addition Reaction of Indoloazomethine Ylides with Arynes for the Synthesis of Thiadiazepine Derivatives

Kim, Dae Kyum; Son, Jeong-Yu; Jung, Ilyong; Heo, Namrim; Han, Sang Hoon; Kim, Dongwook; Lee, Phil Ho

doi:10.1002/adsc.202001310

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Sequential N-Arylation and Intramolecular Imine Addition Reaction of Indoloazomethine Ylides with Arynes for the Synthesis of Thiadiazepine Derivatives

Kim, Dae Kyum;
Son, Jeong-Yu;
Jung, Ilyong;
Heo, Namrim;
Han, Sang Hoon;
외 2명

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3

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3

초록

Metal-free reaction of indoloazomethine ylides with 2-(trimethylsilyl)aryl triflates in the presence of TMAF and MeOH provided 1,4-thiadiazepines through sequential N-arylation and intramolecular imine addition reaction, which is fully oxidized with p-chloranil. These compounds are smoothly isomerized to indoloindolizines in quantitative yield. Moreover, formation of indoloindolizine was accessed from indoloazomethine ylide and 2-(trimethylsilyl)aryl triflate in semi-one-pot.

키워드

indoloazomethine ylide; metal-free; TMAF; thiadiazepine; aryne; SYDNONE DERIVATIVES; POTENT

제목: Sequential N-Arylation and Intramolecular Imine Addition Reaction of Indoloazomethine Ylides with Arynes for the Synthesis of Thiadiazepine Derivatives

저자: Kim, Dae Kyum; Son, Jeong-Yu; Jung, Ilyong; Heo, Namrim; Han, Sang Hoon; Kim, Dongwook; Lee, Phil Ho

DOI: 10.1002/adsc.202001310

발행일: 2021-03-02

유형: Article

저널명: Journal für Praktische Chemie

권: 363

호: 5

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