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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
Actions

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Version History

Mar 25, 2020 Version 1

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License

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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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