Title
Synthesis of functionalized pyridazin-3(2**H**)-ones via nucleophilic substitution of hydrogen (<tex>$S_{N}H$</tex>) Synthesis of functionalized pyridazin-3(2**H**)-ones via nucleophilic substitution of hydrogen (<tex>$S_{N}H$</tex>)
Author
Faculty/Department
Faculty of Sciences. Chemistry
Publication type
article
Publication
Washington, D.C. ,
Subject
Chemistry
Source (journal)
Organic letters / American Chemical Society. - Washington, D.C.
Volume/pages
13(2011) :2 , p. 272-275
ISSN
1523-7060
ISI
000286130000026
Carrier
E
Target language
English (eng)
Full text (Publishers DOI)
Affiliation
University of Antwerp
Abstract
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).
E-info
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