214556-07-7

Upstream product

• 933-76-6 4,5-dichloro-2-methyl-3(2H)-pyridazinone 
• 108-95-2 phenol 
• 212622-34-9 5-chloro-4-phenoxypyridazin-6-one 
• 74-88-4 methyl iodide 
• 139-02-6 sodium phenoxide 

Relevant academic research and scientific papers

Synthesis of 5H-pyridazino[4,5-b]indoles and their benzofurane analogues utilizing an intramolecular Heck-type reaction

The title ring systems were prepared from pyridazin-3(2H)-one precursors in novel, efficient pathways. 2-Methylbenzo[b]furo[2,3-d]pyridazin-1(2H)-one was synthesized via a regioselective nucleophilic substitution reaction of a 2-methyl-4,5-dihalopyridazin-3(2H)-one with phenol followed by an intramolecular Heck-type reaction. The same molecule and its 6-phenyl analogue were also prepared via reaction of 2-methyl-5-iodopyridazin-3(2H)-one or 2-methyl-5-chloro-6-phenylpyridazin-3(2H)-one, respectively, with 2-bromophenol or 2-iodophenol followed by Pd-catalyzed cyclodehydrohalogenation. Moreover, a new approach for the synthesis of 2-methyl-2,5-dihydro-1H-pyridazino[4,5-b] indol-1-ones was also elaborated utilizing a Heck-type ring closure reaction on 5-[(2-bromophenyl)amino]-2-methylpyridazin-3(2H)-ones which were obtained via Buchwald-Hartwig amination of 2-methyl-5-halopyridazin-3(2H)-ones with 2-bromoaniline.

Dehalogenation of 1-Methyl-5-halo-4-substituted-pyridazin-6-ones

In order to confirm the regiochemistry for the functionalization of 1-(1,1-dibromo-2-oxopropyl)-4,5-dihalopyridazin-6-ones, the dehalogenation of 1-methyl-5-halo-4-substituted-pyridazin-6-ones using Pd/C and hydrogen was carried out. The results of the title reaction are reported.