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Synlett 2015; 26(09): 1195-1200
DOI: 10.1055/s-0034-1380348
letter
© Georg Thieme Verlag Stuttgart · New York

Synthesis and Antimicrobial/Cytotoxic Assessment of Ferrocenyl Oxazinanes, Oxazinan-2-ones, and Tetrahydropyrimidin-2-ones

Anka Pejović
a   SynBioC Research Group, Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 9000 Ghent, Belgium
b   Department of Chemistry, Faculty of Science, University of Kragujevac, R. Domanovića 12, 34000 Kragujevac, Serbia
,
Barbara Danneels
c   Centre for Industrial Biotechnology and Biocatalysis, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 9000 Ghent, Belgium
,
Tom Desmet
c   Centre for Industrial Biotechnology and Biocatalysis, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 9000 Ghent, Belgium
,
Ba Thi Cham
d   Institute of Chemistry, Vietnam Academy of Science and Technology, 18-Hoang Quoc Viet, Cau Giay, Hanoi, Vietnam
,
Tuyen Van Nguyen
d   Institute of Chemistry, Vietnam Academy of Science and Technology, 18-Hoang Quoc Viet, Cau Giay, Hanoi, Vietnam
,
Niko S. Radulović
e   Department of Chemistry, Faculty of Science and Mathematics, University of Niš, Visegradska 33, 18000 Niš, Serbia
,
Rastko D. Vukićević*
b   Department of Chemistry, Faculty of Science, University of Kragujevac, R. Domanovića 12, 34000 Kragujevac, Serbia
,
Matthias D’hooghe*
a   SynBioC Research Group, Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 9000 Ghent, Belgium
› Author Affiliations
Further Information

Publication History

Received: 12 January 2015

Accepted after revision: 16 February 2015

Publication Date:
19 March 2015 (online)

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Abstract

3-Arylamino-1-ferrocenylpropan-1-ones, prepared through aza-Michael addition of aromatic amines to 1-ferrocenylpropenone, were transformed into the corresponding 1,3-amino alcohols upon NaBH4-mediated carbonyl reduction. The latter amino alcohols were deployed as eligible substrates for the synthesis of a variety of ferrocene-containing heterocycles including 1,3-oxazinanes, 1,3-oxazinan-2-ones, and tetrahydropyrimidin-2-ones, which were subsequently evaluated for their antimicrobial and cytotoxic activities.

Key words

ferrocenes - heterocycles - oxazinanes - oxazinan-2-ones - tetrahydropyrimidin-2-ones - cyclization - amino alcohols
 

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