Direct Synthesis of Dihydropyrrolo[2,1‐a]Isoquinolines through FeCl3 Promoted Oxidative Aromatization

Direct Synthesis of Dihydropyrrolo[2,1‐a]Isoquinolines through FeCl3 Promoted Oxidative Aromatization

We have developed a straightforward FeCl3 promoted synthesis of dihydropyrrolo[2,1‐a]isoquinolines through formal (3+2) cycloaddition/oxidative aromatization cascade of dihydroisoquinoline with Morita‐Baylis‐Hillman carbonates (up to 96% yield). Further modifications of the obtained products were su...

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Veröffentlicht in:Advanced synthesis & catalysis 2019-10, Vol.361 (20), p.4772-4780
Hauptverfasser: Cui, Hai‐Lei, Jiang, Lu, Tan, Hao, Liu, Si
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Sprache:eng
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Dihydroisoquinoline
Iron Chloride
Morita-Baylis-Hillman carbonates
Oxidative aromatization
Pyrroloisoquinoline
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container_issue 20
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container_title Advanced synthesis & catalysis
container_volume 361
creator Cui, Hai‐Lei
Jiang, Lu
Tan, Hao
Liu, Si
description We have developed a straightforward FeCl3 promoted synthesis of dihydropyrrolo[2,1‐a]isoquinolines through formal (3+2) cycloaddition/oxidative aromatization cascade of dihydroisoquinoline with Morita‐Baylis‐Hillman carbonates (up to 96% yield). Further modifications of the obtained products were successful through simple chemical transformations providing a diverse range of natural product‐like molecules (12 examples).
doi_str_mv 10.1002/adsc.201900756
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source Wiley Online Library Journals Frontfile Complete
subjects Dihydroisoquinoline
Iron Chloride
Morita-Baylis-Hillman carbonates
Oxidative aromatization
Pyrroloisoquinoline
title Direct Synthesis of Dihydropyrrolo[2,1‐a]Isoquinolines through FeCl3 Promoted Oxidative Aromatization
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