Alkylation of pyrimidine derivatives with ethylene chlorohydrin

Krivonogov, V. P.; Мышкин, В. А.; Kozlova, G. G.; Chernyshenko, Yu. N.; Савлуков, А. И.; Плечев, В В; Ibatullina, R. B.; Абдрахманов, И. Б.; Спирихин, Л. В.

doi:10.1134/s1070428006110182

Cited by 2 publications

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“…Recently, Krivogonov et al showed that alkylation of uracils with 2-chloroethanol (2CE) in water-ethanol in the presence of a large excess of potassium hydroxide runs mainly towards formation of dialkylation products accompanied by N3-and not N1-alkyluracils (Table 3). 62 The product tructures were established using 1 H NMR and UV/Vis spectroscopy.…”

Section: Alkylation Of Uracils With Selected Electrophilesmentioning

confidence: 99%

Michael-type Addition as a Convenient Method for Regioselective N-Alkylation of Ambident Uracils

Boncel¹,

Gondela²,

Walczak³

2010

Synthesis

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A review of the Michael-type addition as one of the convenient synthetic methods to N-functionalisation of the uracil ring -against the background of other typical alkylation methods -is presented. The topic of N1-versus N3-regioselectivity in alkylation reactions is emphasised since this differentiation is essential in the various, especially medicinal, applications of substituted uracils. Specifically, the addition of uracils to acrylic acceptors at the N1-position is frequently used in the first stage of the synthesis of pyrimidinic acyclic nucleosides. In turn, the N3-position of the uracil ring is useful in further transformations, like anchoring of biologically active fragments in conjugates for radiochemotherapy or carriage of covalently bonded drug molecules. Nevertheless, N3-substituted derivatives of pyrimidine nucleosides can, themselves, play various therapeutic roles. Fundamental theoretical premises are also detailed, with regard to the rationale behind the orientation of alkylation.

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Section: Alkylation Of Uracils With Selected Electrophilesmentioning

confidence: 99%