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Synthesis 2008(2): 304-310  
DOI: 10.1055/s-2007-990948
PAPER
© Georg Thieme Verlag Stuttgart · New York

Chemistry of Polyhalogenated Nitrobutadienes, 6: A New Ring-Closure Approach to Perfunctionalized 5-Nitropyrimidines

Viktor A. Zapol’skiia, Jan C. Namysloa, Cevher Altuga, Mimoza Gjikajb, Dieter E. Kaufmann*a
a Institute of Organic Chemistry, Clausthal University of Technology, Leibnizstr. 6, 38678 Clausthal-Zellerfeld, Germany
Fax: +49(5323)722834; e-Mail: dieter.kaufmann@tu-clausthal.de;
b Institute of Inorganic and Analytical Chemistry, Clausthal University of Technology, Paul-Ernst-Str. 4, 38678 Clausthal-Zellerfeld, Germany
Further Information

Publication History

Received 24 August 2007
Publication Date:
07 December 2007 (online)

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Abstract

The recently reported capability of pentachloro-2-nitro­butadiene and some closely related derivatives to allow the synthesis of highly substituted acyclic as well as five-membered (hetero)cyclic compounds is herein extended to pyrimidines with an exceptional substitution pattern. Our novel approach starts from a 1,1-diamino-3,4,4-trichloro-2-nitrobuta-1,3-diene and an appropriate amidine. Some of the resulting perfunctionalized pyrimidines were subjected to further transformations to give promising candidates with respect to biological, especially pharmacological, activity.

Key words

nitro compounds - halides - pyrimidines - ring closure - nucleophilic substitution

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3

All data of C10H12Cl2N4O3 were collected on a Stoe IPDS-II single-crystal X-ray diffractometer with graphite monochromated MoKα radiation (λ = 0.71073 Å) at 223 K. The crystal structure was solved by direct methods and refined by full matrix least squares on F 2 (SHELX-97)4 in the triclinic space group P1 (Nr. 2), lattice parameters a = 921.5(3) pm, b = 1230.6(5) pm, c = 1369.6(6) pm, V = 1315.1(9) × 106 pm3, Z = 4, d calc = 1.551 g cm-3, F(000) = 632, absorption coefficient = 0.503 mm-1 using 4346 independent reflections and 439 parameters. R1 = 0.0420, wR2 = 0.1011 [I > 2σ(I)], goodness of fit on F 2 = 1.082, residual electronic density = 0.463 and -0.341 e A-3. Crystallographic data have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-645171. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44(1223)336033, e-mail: fileserv@ccdc.ac.uk or http://www.ccdc.cam.ac.uk).

4

Sheldrick, G. M. SHELX-97; University of Göttingen, 1997.