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

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-p...

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Published in:Synthesis (Stuttgart) 2007-03, Vol.2007 (6), p.835-844
Main Authors: Sukach, Volodymyr A., Bol’but, Andriy V., Petin, Alexander Yu, Vovk, Mykhaylo V.
Format: Article
Language:English
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Summary: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.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-2007-965933