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

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

References

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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: [phone], e-mail: [e-mail] or http://www.ccdc.cam.ac.uk).

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