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Synthesis of 1-pyrroline 1-oxides analogous to pseudouridine

✍ Scribed by Mariola Koszytkowska-Stawińska; Ewa Mironiuk-Puchalska; Wojciech Sas

Publisher
Elsevier Science
Year
2011
Tongue
French
Weight
303 KB
Volume
52
Category
Article
ISSN
0040-4039

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✦ Synopsis

a b s t r a c t Pseudouridine (w-uridine, W) aza 0 -analogues with a 5,5-bis(hydroxymethyl)-1-pyrrolin-2-yl 1-oxide as the glycone mimic were obtained by the addition of (2,4-dimethoxypyrimidin-5-yl)magnesium bromide to 1-aza-7,14-dioxadispiro[4.2.5.2]pentadec-1-ene 1-oxide (3), followed by oxidation and removal of the protecting groups. The analogous synthesis from (2,4-dimethoxypyrimidin-5-yl)lithium and 3 was less efficient; in the first step of the reaction sequence, competing dimerisation of 3 predominated over addition of the organolithium agent to 3.

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## Abstract ^13^C NMR data for forty 1‐pyrroline 1‐oxides, six __2H__‐pyrrole 1‐oxides, three __2H__‐pyrroles, eight 1‐pyrrolines and four related oxaziridines are reported. Comparisons are made with respect to the five‐membered ring carbons, subdividing them as the central carbons, the nitrone car