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Title
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Synthesis of functionalized pyridazin-3(2H)-ones via selective bromine-magnesium exchange and lactam directed ortho C-H magnesiation
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Author
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Abstract
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| Selective bromine-magnesium exchange on 2-benzyl-5-bromo-4-methoxypyridazin-3(2H)-one could be achieved when MesMgBr was used as reagent. With more nucleophilic RMgCl species (R = Bu, i-Pr, and Ph) both nucleophilic addition-elimination at C-4 and bromine-magnesium exchange at C-5 occurred. In 2-benzyl-5-bromopyridazin-3(2H)-one, which does not contain a substituent at C-4, addition could not be suppressed. Less nucleophilic Mg amides (TMPMgCl.LiCl) allowed regioselective C-H magnesiation at the C-4 position in such substrates, as exemplified for 2-benzyl-5-chloro- and 2-benzyl-6-chloropyridazin-3(2H)-one. Quenching of the magnesiated pyridazinonens with electrophiles gives access to a variety of hitherto unknown pyridazin-3(2H)-one derivatives. |
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Language
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English
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Source (journal)
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The journal of organic chemistry. - Washington, D.C., 1936, currens
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Publication
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Washington, D.C.
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2011
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ISSN
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0022-3263
[print]
1520-6904
[online]
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DOI
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10.1021/JO201009M
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Volume/pages
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76
:16
(2011)
, p. 6670-6677
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ISI
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000293759000020
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Full text (Publisher's DOI)
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