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Iron Catalyzed Formal [3+2] Cycloaddition of Tetrahydroisoquinoline Affording Amide-bearing Dihydropyrrolo[2,1-a]isoquinolines

25 March 2020, Version 1
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

We have developed an iron(III) chloride hexahydrate catalyzed formal [3+2] cycloaddition of tetrahydroisoquinolines with amide group-bearing Morita-Baylis-Hillman (MBH) carbonates. A range of highly functionalized dihydropyrrolo[2,1-a]isoquinolines could be prepared through SN2’/oxidation/ electrocyclization/aromatization cascade (32-62% yield).


Keywords

Iron chloride
dihydropyrrolo[2,1-a]isoquinoline
cycloaddition
tetrahydroisoquinoline

Supplementary materials

Title
Description
Actions
Title
191118CHL 0m
Description
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Now Published

Iron Catalyzed [3+2] Cycloaddition of Tetrahydroisoquinoline: Synthesis of Dihydropyrrolo[2,1‐a]isoquinolines [opens in a new tab]
Si‐Wei Liu, Dan‐Dan Ma, Xin‐Xin Zhu, Cheng‐Dan Luo, Hui‐Lin Tan, Xiao‐Li Ju, Xue Tan, Xiao‐Hui Tang, Jie Huang, Jia Wang, Xian‐Xun Wang, Hai‐Lei Cui journal article
Asian Journal of Organic Chemistry , Volume 9, Issue 10
Online publication date: Jul 20, 2020

Version History

Mar 25, 2020 Version 1

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The content is available under CC BY NC 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv.12015651.v1
D O I: 10.26434/chemrxiv.12015651.v1 [opens in a new tab]

Funding

the National Natural Science Foundation of China (21871035, 21502013)

Author’s competing interest statement

No conflict of interest.

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