Synthesis of Indole-Dihydroisoquinoline Sulfonyl Ureas via Three-Component Reactions

Stuart E. Pearson; Shaun M. Fillery; Kristin Goldberg; Julie E. Demeritt; Jonathan Eden; Jonathan Finlayson; Anil Patel

doi:10.1055/s-0037-1610223

Synthesis, Table of Contents

Synthesis 2018; 50(24): 4963-4981
DOI: 10.1055/s-0037-1610223

paper

Synthesis of Indole-Dihydroisoquinoline Sulfonyl Ureas via Three-Component Reactions

Stuart E. Pearson*

^aMedicinal Chemistry, Oncology, IMED Biotech Unit, AstraZeneca, Cambridge, UK Email: stuart.pearson@astrazeneca.com

,

Shaun M. Fillery

^aMedicinal Chemistry, Oncology, IMED Biotech Unit, AstraZeneca, Cambridge, UK Email: stuart.pearson@astrazeneca.com

,

Kristin Goldberg

^aMedicinal Chemistry, Oncology, IMED Biotech Unit, AstraZeneca, Cambridge, UK Email: stuart.pearson@astrazeneca.com

,

Julie E. Demeritt

^bFormerly of Oncology Innovative Medicines, AstraZeneca, Mereside, Alderley Park, Macclesﬁeld, Cheshire SK10 4TG, UK

,

Jonathan Eden

^bFormerly of Oncology Innovative Medicines, AstraZeneca, Mereside, Alderley Park, Macclesﬁeld, Cheshire SK10 4TG, UK

,

Jonathan Finlayson

^bFormerly of Oncology Innovative Medicines, AstraZeneca, Mereside, Alderley Park, Macclesﬁeld, Cheshire SK10 4TG, UK

,

Anil Patel

^bFormerly of Oncology Innovative Medicines, AstraZeneca, Mereside, Alderley Park, Macclesﬁeld, Cheshire SK10 4TG, UK

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Abstract

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Abstract

Isoquinolines activated with sulfamoyl chlorides were reacted with indoles in a 3-component reaction to generate a library of dihydroisoquinoline derivatives. Using a differential protecting group strategy, products could be further derivatised. Synthesis of isoquinoline starting materials using several different methods is also described.

Key words

multicomponent reaction - combinatorial chemistry - isoquinolines - indoles - sulfonamides

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References

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