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A Convenient Synthesis of 1-(omega-Aminoalkyl)-5-nitro-1H-pyrimidine-2,4-diones

Węgrzynek E., Walczak K.

Polish Journal of Chemistry

2009

Vol. 83, nr 1

57-64

Several monoacylated alkylene diamines have been obtained in the reaction of appropriate amine with methyl phenylacetate or ethyl formate. The monoprotected diamines were used as alkylating agents in reactions with 1-(2,4-dinitrophenyl)-5-nitrouracil. The series of hitherto unknown 1-(w-aminoalkyl)-5-nitrouracil derivatives have been obtained as a result of the uracil ring transformation. The best yield of 1-(omega-aminoalkyl)- 5-nitro - uracils was obtained when N-Boc protected alkylene diamines were applied in this reaction. The N-Boc protecting group was cleaved using diluted trifluoroacetic acid, and the liberated amines were subjected to reaction with phthalic anhydride and naphthalene 1,8-dicarboxylic anhydride.

1-(2,4-Dinitrophenyl)-5-nitrouracil a Versatile Reagent for the Synthesis of N1-Modified Uracil Derivatives

Gondela A., Sroka M., Walczak K.

Polish Journal of Chemistry

2007

Vol. 81, nr 12

2143-2149

1-(2,4-Dinitrophenyl)-5-nitrouracil has been used as a substrate in reactions with a number of compounds possessing primary amino groups such as: amino alcohols, aminodiols, esters of amino ac ids and benzylamines. As a result of regioselective course of performed reactions the series of 5-nitro-1-substituted uracils were obtained. All newly synthesized compounds were subjected to primary bioactivity as says as inhibitors against Mycobacterium tuberculosis; two of them exhibited inhibition ability.

Hydroksyalkilowanie 5-podstawionych pochodnych uracylu

Gondela A., Walczak K.

Chemik

2005

Vol. 58, nr 6

325-326

Opisano metodę N-alkilowania 5-podstawionych pochodnych uracylu przy pomocy pierwszorzędowych amin alifatycznych zawierających grupę hydroksylową. Reakcja alkilowania zachodzi według mechanizmu typu ANRORC.

5-Substituted uracil derivatives have been N-alkylated using primary hydroxyalkylamines. The alkylation reaction proceeds according to the ANRORC type mechanism.