Synthesis 2016; 48(08): 1122-1130
DOI: 10.1055/s-0035-1561353
paper
© Georg Thieme Verlag Stuttgart · New York

Hydrazine in the Ugi Tetrazole Reaction

Pravin Patil
a   University of Groningen, Department of Drug Design, A. Deusinglaan 1, 9713 AV Groningen, The Netherlands   Email: a.s.s.domling@rug.nl
,
Ji Zhang
a   University of Groningen, Department of Drug Design, A. Deusinglaan 1, 9713 AV Groningen, The Netherlands   Email: a.s.s.domling@rug.nl
,
Katarzyna Kurpiewska
b   Jagiellonian University, Faculty of Chemistry, Department of Crystal Chemistry and Crystal Physics, Biocrystallography Group, Ingardena 3, 30-060 Kraków, Poland
,
Justyna Kalinowska-Tłuścik
b   Jagiellonian University, Faculty of Chemistry, Department of Crystal Chemistry and Crystal Physics, Biocrystallography Group, Ingardena 3, 30-060 Kraków, Poland
,
Alexander Dömling*
a   University of Groningen, Department of Drug Design, A. Deusinglaan 1, 9713 AV Groningen, The Netherlands   Email: a.s.s.domling@rug.nl
› Author Affiliations
Further Information

Publication History

Received: 25 November 2015

Accepted after revision: 08 January 2016

Publication Date:
15 February 2016 (online)


� 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.

Supporting Information