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research article

Synthesis of Triazenes with Nitrous Oxide

Kiefer, Gregor  
•
Riedel, Tina  
•
Dyson, Paul Joseph  
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2015
Angewandte Chemie International Edition

Triazenes are valuable compounds in organic chemistry and numerous applications have been reported. Furthermore, triazenes have been investigated extensively as potential antitumor drugs. Here, we describe a new method for the synthesis of triazenes. The procedure involves a reagent which is rarely used in synthetic organic chemistry: nitrous oxide (N2O, “laughing gas”). Nitrous oxide mediates the coupling of lithium amides and organomagnesium compounds while serving as a nitrogen donor. Despite the very inert character of nitrous oxide, the reactions can be performed in solution under mild conditions. A key advantage of the new procedure is the ability to access triazenes with alkynyl and alkenyl substituents. These compounds are difficult to prepare by conventional methods because the required starting materials are unstable. Some of the new alkynyltriazenes were found to display high cytotoxicity in in vitro tests on ovarian and breast cancer cell lines.

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Type
research article
DOI
10.1002/anie.201408597
Web of Science ID

WOS:000347065100049

Author(s)
Kiefer, Gregor  
Riedel, Tina  
Dyson, Paul Joseph  
Scopelliti, Rosario  
Severin, Kay  
Date Issued

2015

Publisher

Wiley-Blackwell

Published in
Angewandte Chemie International Edition
Volume

54

Start page

302

End page

305

Subjects

amides

•

coupling reactions

•

Grignard reagents

•

nitrous oxide

•

triazenes

Editorial or Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LCS  
LCOM  
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/108096
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