Synthesis of Cyclic Amidines from Quinolines by a Borane-Catalyzed Dearomatization Strategy

Synthesis of Cyclic Amidines from Quinolines by a Borane-Catalyzed Dearomatization Strategy

Described herein is the development of a new synthetic route to cyclic amidines from quinolines. The borane-catalyzed 1,4-hydrosilylation of quinoline was utilized for the dearomatization of the quinolines. The dearomatized enamine intermediate was subsequently reacted with a broad range of organic...

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Veröffentlicht in:Organic letters 2020-01, Vol.22 (2), p.515-519
Hauptverfasser: Cao, Vinh Do, Mun, So Hwa, Kim, Seo Ha, Kim, Gyeong Un, Kim, Hyung Guk, Joung, Seewon
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container_issue 2
container_start_page 515
container_title Organic letters
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creator Cao, Vinh Do
Mun, So Hwa
Kim, Seo Ha
Kim, Gyeong Un
Kim, Hyung Guk
Joung, Seewon
description Described herein is the development of a new synthetic route to cyclic amidines from quinolines. The borane-catalyzed 1,4-hydrosilylation of quinoline was utilized for the dearomatization of the quinolines. The dearomatized enamine intermediate was subsequently reacted with a broad range of organic azides to produce the corresponding cyclic amidines (3,4-dihydroquinolinimines) via a [3 + 2] cycloaddition pathway. Preliminary mechanistic studies suggested that the hydride shift was involved during the cycloaddition.
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title Synthesis of Cyclic Amidines from Quinolines by a Borane-Catalyzed Dearomatization Strategy
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