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Synthesis of site specifically deuterated primaquines II. N-alkyl deuterated primaquines

✍ Scribed by James D. McChesney; Srinivasan Sarangan


Publisher
John Wiley and Sons
Year
1984
Tongue
French
Weight
278 KB
Volume
21
Category
Article
ISSN
0022-2135

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✦ Synopsis


Abstract

Two site specifically deuterated primaquines were prepared. 4′,4′‐Dideutero primaquine 3 was obtained from the corresponding dideutero alcohol which was prepared by the low temperature reduction of the ester compound 4 with lithium aluminium deuteride. 1′‐Deutero primaquine r was prepared by the reductive alkylation of 6‐methoxy‐8‐aminoquinoline with N‐(2‐oxopentyl)‐phthalimide in the presence of sodium cyanoborodeuteride followed by removal of protective phthalimide group.


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Synthesis of site specifically deuterate
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The synthesis of arachidonic acid derivatives containing site-specifically incorporated deuterium atoms and also a remote tritium label are described. Deuterium incorporation at the C11 and/or C15 position was achieved using Wittig chemistry, while the radiolabel was introduced at a remote position