HSAB Driven chemoselectivity in alkylation of uracil derivatives. A high yielding preparation of 3-alkylated and unsymmetrically 1,3-dialkylated uracils
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Synthesis, characterization and theoretical evaluations of HMDS promoted chemoselective O-alkylation of uracils
2013, TetrahedronCitation Excerpt :The tetradentate nucleophilic nature of uracils or their conjugated bases have made their chemoselective alkylation an interesting subject for long debate. Uracils are susceptible to N/O alkylation and as a result a mixture of N1, N1+N3 and some O4-alkyl derivatives are obtained.7 The chemoselectivity in the alkylation of uracils has recently been reviewed by Krzyszto Walezac et al.8 Most chemical efforts has been devoted in uracil participation towards selective N1 and to some extent N3 alkylation while the selective O4-alkylation has been largely overlooked partly because the O-alkyluracil ethers isomerize to their N-alkyl derivatives in the presence of Lewis acids.9,10
HSAB-driven chemoselective N<sup>1</sup>-alkylation of pyrimidine bases and their 4-methoxy- or 4-acetylamino-derivatives
2006, TetrahedronCitation Excerpt :The reactivity was always lower and small amounts of O2-alkylation products were always present, even in methylations. This is not unexpected25 and could be related to the weaker electron releasing effect of the acetylamino group, resulting in a smaller difference in hardness between O2 and N1. In contrast, the use of DMF, where loose O−Li+ pairs were expected, gave rise to a considerable amount of O2-alkylation, which increased with the hardness of the electrophile (compare runs 6, 16 and 26 with runs 8, 18 and 28, respectively).
Highly efficient protocol for one-pot N-alkylation of nucleobases using alcohols in bmim[Br]: A rapid route to access acyclic nucleosides
2015, Journal of the Iranian Chemical Society