Synlett 2014; 25(14): 2001-2004
DOI: 10.1055/s-0033-1338655
letter
© Georg Thieme Verlag Stuttgart · New York

α-Azido Ketones, Part 8: Base-Induced Coupling of α-Azido Ketones with a 1,2-Diaza-1,3-diene as a Michael Acceptor[1]

Éva Juhász-Tóth
a  Department of Organic Chemistry, University of Debrecen, Egyetem tér 1, 4032 Debrecen, Hungary   Fax: +36-52-512744   Email: patonay.tamas@science.unideb.hu
,
Gianfranco Favi
b  Department of Biomolecular Sciences, Section COCON, University of Urbino ‘Carlo Bo’, Via I Maggetti 24, 61029 Urbino, Italy
,
Orazio A. Attanasi
b  Department of Biomolecular Sciences, Section COCON, University of Urbino ‘Carlo Bo’, Via I Maggetti 24, 61029 Urbino, Italy
,
Attila C. Bényei
c  Laboratory for X-ray Diffraction, Department of Pharmaceutical Chemistry, University of Debrecen, Egyetem tér 1, 4032 Debrecen, Hungary
,
Tamás Patonay*
a  Department of Organic Chemistry, University of Debrecen, Egyetem tér 1, 4032 Debrecen, Hungary   Fax: +36-52-512744   Email: patonay.tamas@science.unideb.hu
› Author Affiliations
Further Information

Publication History

Received: 18 April 2014

Accepted: 31 May 2014

Publication Date:
28 July 2014 (online)

Abstract

Carbanions generated from various acyclic and cyclic α-azido ketones in the presence of bases were reacted with ethyl 3-[(carbamoylimino)amino]but-2-enoate as a Michael acceptor to give the corresponding adducts. The adducts of acyclic azides were unstable and eliminated hydrazoic acid to give the corresponding ethyl 2-[1-[(carbamoylamino)imino]ethyl]-4-oxo-4-phenylbut-2-enoates as (E,E/Z,E)-diastereomeric mixtures. The relative configuration of these diastereomers was determined by X-ray analysis. Adducts of cyclic α-azido ketones were obtained in diastereomerically pure form, with the exception of 2-azidobenzosuberone.

Supporting Information

 
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