Tewoderos M Ayele, Stephanie J. Chang, Marino J. E. Resendiz
Jul 22, 2015
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Influential Citations
4
Citations
Journal
Tetrahedron Letters
Abstract
Abstract The use of seven N,N-dimethylformamide dialkyl acetals (methyl-, ethyl-, benzyl-, n-propyl-, n-butyl-, t-butyl, and neopentyl-) was explored for the exocyclic amine protection and subsequent N-alkylation of 8-oxoadenosine and guanosine. Reactions occurred in good to modest yields (50–95%) upon addition of heat (60 °C) using DMF as solvent. We determined relative rates of reaction and kinetic experiments resulted in the following order: Me ≫ Bn ≈ t-Bu ≫ Et ≈ n-Pr ≈ n-Bu > Me (Np, neopentyl). We found that groups that stabilize a pseudo-carbocation intermediate facilitate the completion of the reaction and lead to different reaction pathways, including elimination of isobutylene and ethylene in some cases.