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

doi:10.1055/S-2007-965933

Paper

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

Published Mar 1, 2007 · V. Sukach, A. V. Bol’but, A. Y. Petin

Synthesis

Q2 SJR score

3

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0

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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(1 H)-ones, 8-nitro-2,3,6,7-tetrahydroimidazo[1,2-c]pyrimidin-5(1 H)-ones and 9-nitro-1,2,3,4,7,8-hexahydro-6 H-pyrimido[1,6-a]pyrimidin-6(1 H)-ones. Substitution of the methylthio group in 6-methylthio-5-nitro-3,4-dihydropyrimidin-2(1 H)-ones provided 6-amino-5-nitro-3,4-dihydropyrimidin-2(1 H)-ones, which exist in tautomeric equilibrium with 4-imino-5-nitro-3,4,5,6-tetrahydropyrimidin-2(1 H)-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(1 H)-ones.

Study Snapshot

Cyclocondensation of 1-chlorobenzyl isocyanates with S, N-, and N, N-nitroketeneacetals allows the synthesis of novel functionalized derivatives of 5-Nitro-3,4-dihydropyrimidin-2(1H)-one

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

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

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References

Citations

One-Pot Synthesis of 4-Sulfonyliminotetrahydropyrimidin-2-one Derivatives through a Copper-Catalyzed Tandem Reaction.

Copper-catalyzed tandem reaction efficiently synthesizes a wide range of polysubstituted 4-sulfonyliminotetrahydropyrimidin-2-ones in one pot, potentially benefiting biological chemistry and medicinal science.

Chemistry of Ketene N,S-Acetals: An Overview.

Ketene N,S-acetals are versatile building blocks in organic synthesis, with applications in various heterocyclic systems and related natural products.

Pyrrole- and dihydropyrrole-fused neonicotinoids: design, synthesis, and insecticidal evaluation.

Pyrrole- and dihydropyrrole-fused neonicotinoids show excellent insecticidal activity against cowpea aphids, offering potential for use in agricultural pest control.