Publication
Title
Synthesis of functionalized pyridazin-3(2**H**)-ones via nucleophilic substitution of hydrogen ()
Author
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).
Language
English
Source (journal)
Organic letters / American Chemical Society. - Washington, D.C.
Publication
Washington, D.C. : 2011
ISSN
1523-7060
Volume/pages
13:2(2011), p. 272-275
ISI
000286130000026
Full text (Publishers DOI)
Full text (publishers version - intranet only)
UAntwerpen
Faculty/Department
Research group
Publication type
Subject
Affiliation
Publications with a UAntwerp address
External links
Web of Science
Record
Identification
Creation 02.02.2011
Last edited 25.05.2017
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