Selective alkylation at the N1 position of thymine and uracil in the Mitsunobu system

被引：0

作者：

Soares, Fabio D. P. ^{[1
]}

de Siqueira, Edmilson C. ^{[1
]}

do Nascimento, Sandra A. ^{[1
]}

Doboszewski, Bogdan ^{[1
]}

机构：

[1] Univ Fed Rural Pernambuco, Dept Quim, R Manoel Medeiros S-N, BR-52717900 Recife, PE, Brazil

来源：

ORBITAL-THE ELECTRONIC JOURNAL OF CHEMISTRY | 2010年 / 2卷

关键词：

alkylation; Mitsunobu system; pyrimidine; selectivity;

D O I：

暂无

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Selectivity of alkylation at the N1 position in pyrimidines (thymine and uracil) was achieved by the application of N3-benzoyl thymine and N3-benzoyl uracil as substrates, where the N3 atom was temporarily protected, exposing the N1 atom as the alkylation site. The N3-benzoylated compounds were obtained by double benzoylation at the N1 and N3 positions, and selective basic hydrolysis at the N1 atom. Using the Mitsunobu conditions (iPrO(2)CN= NCO(2)iPr, Ph3P, ROH) both pyrimidines were reacted with allyl and propargyl alcohol. To avoid difficulties during purification of the N1-alkyl N3-benzoylated intermediates, basic hydrolysis was realized to remove the N3- benzoyl group, since this facilitates the separation of final products from triphenylphosphine oxide and iPrO(2)CNHNHCO(2)iPr. N1-Allyl and - propargyl thymine and uracil are the substrates for future transformations.

引用

页码：1 / 10

页数：10