Study of Oxidative Cyclization Using PhI(OAc)2 in the Formation of Benzo[4,5]thiazolo[2,3-c][1,2,4]triazoles and Related Heterocycles – Scope and 
Limitations

Charles S. Demmer; Morten Jørgensen; Jan Kehler; Lennart Bunch

doi:10.1055/s-0033-1341159

Synlett, Table of Contents

Synlett 2014; 25(09): 1279-1282
DOI: 10.1055/s-0033-1341159

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Study of Oxidative Cyclization Using PhI(OAc)₂ in the Formation of Benzo[4,5]thiazolo[2,3-c][1,2,4]triazoles and Related Heterocycles – Scope and Limitations

Charles S. Demmer*

^aMedicinal Chemistry Research, H. Lundbeck A/S, 9 Ottiliavej, 2500 Valby, Denmark

^bChemical Neuroscience Group, Department of Drug Design and Pharmacology, Faculty of Health and Medical Sciences, University of Copenhagen, Universitetsparken 2, 2100 Copenhagen, Denmark Email: charles.demmer@sund.ku.dk Email: cdemmer15@gmail.com

,

Morten Jørgensen

^aMedicinal Chemistry Research, H. Lundbeck A/S, 9 Ottiliavej, 2500 Valby, Denmark

,

Jan Kehler

^aMedicinal Chemistry Research, H. Lundbeck A/S, 9 Ottiliavej, 2500 Valby, Denmark

,

Lennart Bunch

^bChemical Neuroscience Group, Department of Drug Design and Pharmacology, Faculty of Health and Medical Sciences, University of Copenhagen, Universitetsparken 2, 2100 Copenhagen, Denmark Email: charles.demmer@sund.ku.dk Email: cdemmer15@gmail.com

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Abstract

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Abstract

A one-pot, two-step reaction for the synthesis of benzo[4,5]thiazolo[2,3-c][1,2,4]triazoles and related heterocycles under mild conditions was herein developed. The key step of this transformation is an oxidative cyclization employing PhI(OAc)₂ as reagent. Scope and limitations (group functionality tolerance and sterics) were studied showing the robustness of the present methodology which can be used as potential access to new fused heterocycle libraries.

Key words

cyclization - heterocycles - fused-ring systems - substituent effects - condensation

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References

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Supplementary Material

Supporting Information

Study of Oxidative Cyclization Using PhI(OAc)2 in the Formation of Benzo[4,5]thiazolo[2,3-c][1,2,4]triazoles and Related Heterocycles – Scope and Limitations

Study of Oxidative Cyclization Using PhI(OAc)₂ in the Formation of Benzo[4,5]thiazolo[2,3-c][1,2,4]triazoles and Related Heterocycles – Scope and Limitations