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Synthesis 2007(6): 835-844  
DOI: 10.1055/s-2007-965933
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Novel Functionalized Derivatives of 5-Nitro-3,4-dihydropyrimidin-2(1H)-one by the Cyclocondensation of 1-Chlorobenzyl Isocyanates with N,S- and N,N-Nitroketeneacetals

Volodymyr A. Sukacha, Andriy V. Bol’buta, Alexander Yu. Petinb, Mykhaylo V. Vovk*a
a Institute of Organic Chemistry National Academy of Science of Ukraine, Murmans’ka 5, 02094 Kiev, Ukraine
b Research and Development Center for Chemistry and Biology, National Taras Shevchenko University, Volodymyrs’ka 62, 01033 Kiev, Ukraine
Fax: +380(44)5732643; e-Mail: mvovk@i.com.ua;
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Publication History

Received 7 September 2006
Publication Date:
13 February 2007 (online)

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Abstract

The cyclocondensation of 1-chlorobenzyl isocyanates with S,N- and N,N-nitroketeneacetals has been employed to synthesize hitherto-unknown 6-methylthio-5-nitro-3,4-dihydropyrimidin-2(1H)-ones, 8-nitro-2,3,6,7-tetrahydroimidazo[1,2-c]pyrimidin-5(1H)-ones and 9-nitro-1,2,3,4,7,8-hexahydro-6H-pyrimido[1,6-a]pyrimidin-6(1H)-ones. Substitution of the methylthio group in 6-methylthio-5-nitro-3,4-dihydropyrimidin-2(1H)-ones provided 6-amino-5-nitro-3,4-dihydropyrimidin-2(1H)-ones, which exist in tautomeric equilibrium with 4-imino-5-nitro-3,4,5,6-tetrahydropyrimidin-2(1H)-ones. The compounds obtained, if boiled in dioxane in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), eliminate the nitro groups to give substituted 4-imino-3,4-dihydropyrimidin-2(1H)-ones.

Key words

heterocyclization - tautomerism - 1-chlorobenzyl isocyanates - S,N- and N,N-nitroketeneacetals - 3,4-dihydropyrimidones