Synthesis of Pyridazine Dicarboxamides via Highly Selective Palladium-catalyzed Aminocarbonylation

Szőke, Gyöngyi and Takács, Attila and Kollár, László (2016) Synthesis of Pyridazine Dicarboxamides via Highly Selective Palladium-catalyzed Aminocarbonylation. Journal of Heterocyclic Chemistry, 53. pp. 2020-2024. ISSN 0022-152X, ESSN: 1943-5193

Text JHeterocyclChem_pyridazine.pdf Restricted to Repository staff only Download (338kB) | Request a copy

Abstract

Highly selective palladium-catalyzed aminocarbonylation of 3,6-diiodopyridazine with various primary and secondary amines including amino acid esters was carried out. Because of the simple carbon monoxide insertion regarding both iodoarene functionalities, the corresponding 3,6-diamides were synthesized in moderate to high yields. The exclusive formation of amides, that is, the missing of 2-ketoamides which might be formed via double carbon monoxide insertion, can be explained by the close proximity of the nitrogen of the aromatic ring to the iodo substituent. The unexpected selectivity of the aminocarbonylation is rationalized by a mechanistic approach.

Actions (login required)

Edit Item