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Title
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Synthesis of functionalized pyridazin-3(2**H**)-ones via nucleophilic substitution of hydrogen ()
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Author
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Abstract
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| Reaction of 2-benzyl-5-halopyridazin-3(2H)-ones (3) with Grignard reagents followed by quenching with electrophiles unexpectedly yielded 4,5-disubstituted pyridazin-3(2H)-ones instead of 5-substituted pyridazin-3(2H)-ones. These reactions represent the first examples of cine substitution in which the anionic σH-adduct is quenched by electrophiles (other than a proton) before elimination takes place. Insight into the reaction mechanism led to the direct transformation of 2-benzylpyridazin-3(2H)-one (7) and 2-benzyl-6-chloropyridazin-3(2H)-one (9) into the corresponding C-4 alkyl and aryl derivatives (when Br2 was used as the electrophile). |
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Language
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English
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Source (journal)
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Organic letters / American Chemical Society. - Washington, D.C.
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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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1523-7060
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DOI
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10.1021/OL102703W
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Volume/pages
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13
:2
(2011)
, p. 272-275
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ISI
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000286130000026
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Full text (Publisher's DOI)
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Full text (publisher's version - intranet only)
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