Tosylation/mesylation of 4-hydroxy-3-nitro-2-pyridinones as an activation step in the construction of dihydropyrido[3,4- b] benzo[ f][1,4]thiazepin-1-one based anti-HIV agents

[Display omitted] Reaction of 4-hydroxy-3-nitropyridinone 8 with TsCl and MsCl, respectively, resulted in rapid and quantitative formation of ditosylate 13 and dimesylate 16 . Through chemoselective reaction of 16 with thiophenol 17 the key 4-thioaryl substituted intermediate 18 was obtained in 78%...

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Bibliographic Details
Published in:Tetrahedron letters 2005-04, Vol.46 (16), p.2919-2922
Main Authors: Storck, Pierre, Aubertin, Anne-Marie, Grierson, David S.
Format: Article
Language:English
Subjects:
Anti-HIV
Dihydropyridobenzothiazepin-1-ones
Mesylation
Pyridinones
Reverse transcriptase
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Summary:[Display omitted] Reaction of 4-hydroxy-3-nitropyridinone 8 with TsCl and MsCl, respectively, resulted in rapid and quantitative formation of ditosylate 13 and dimesylate 16 . Through chemoselective reaction of 16 with thiophenol 17 the key 4-thioaryl substituted intermediate 18 was obtained in 78% yield. This compound was efficiently converted to the target tricyclic products 4a and b . Compound 4a , in particular, is a potent inhibitor in vitro (IC 50 = 2 nM) of wild type HIV-1 replication.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2005.02.128