Hydrazine in the Ugi Tetrazole Reaction

Pravin Patil; Ji Zhang; Katarzyna Kurpiewska; Justyna Kalinowska-Tłuścik; Alexander Dömling

doi:10.1055/s-0035-1561353

Synthesis, Table of Contents

Synthesis 2016; 48(08): 1122-1130
DOI: 10.1055/s-0035-1561353

paper

Hydrazine in the Ugi Tetrazole Reaction

Pravin Patil

^aUniversity of Groningen, Department of Drug Design, A. Deusinglaan 1, 9713 AV Groningen, The Netherlands Email: a.s.s.domling@rug.nl

,

Ji Zhang

^aUniversity of Groningen, Department of Drug Design, A. Deusinglaan 1, 9713 AV Groningen, The Netherlands Email: a.s.s.domling@rug.nl

,

Katarzyna Kurpiewska

^bJagiellonian University, Faculty of Chemistry, Department of Crystal Chemistry and Crystal Physics, Biocrystallography Group, Ingardena 3, 30-060 Kraków, Poland

,

Justyna Kalinowska-Tłuścik

^bJagiellonian University, Faculty of Chemistry, Department of Crystal Chemistry and Crystal Physics, Biocrystallography Group, Ingardena 3, 30-060 Kraków, Poland

,

Alexander Dömling*

^aUniversity of Groningen, Department of Drug Design, A. Deusinglaan 1, 9713 AV Groningen, The Netherlands Email: a.s.s.domling@rug.nl

› Author Affiliations

Abstract

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^◊� The authors contributed equally to the work.

Abstract

We describe the hitherto unknown use of N-Boc-protected hydrazine in the Ugi tetrazole reaction to access a library of highly substituted 5-(hydrazinomethyl)-1-methyl-1H-tetrazoles. The reaction is very versatile and good to high yielding. A one-pot, two-step procedure is given.

Key words

hydrazine - isocyanides - tetrazoles - multicomponent reaction - Ugi reaction

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References

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8 CCDC 1438137 (5a), CCDC 1438135 (5k) and CCDC 1438136 (5n) contain the supplementary crystallographic data for this paper. The data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.

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