Functionalization of the pyridazin-3(2H)-one ring via palladium-catalysed aminocarbonylation |
| |
Authors: | Attila Takács Andrea Czompa Gábor Krajsovszky Péter Mátyus László Kollár |
| |
Affiliation: | 1. Department of Inorganic Chemistry, University of Pécs and János Szentágothai Science Center, H-7624 Pécs, PO Box 266, Hungary;2. Department of Organic Chemistry, Semmelweis University, H?gyes E. u. 7., H-1092 Budapest, Hungary |
| |
Abstract: | 5-Iodo- and 4,5-dibromo-2-methylpyridazin-3(2H)-ones were aminocarbonylated in the presence of various amines including amino acid methyl esters in a palladium-catalysed reaction. The iodo derivative afforded the corresponding amides with complete conversion and high isolated yields. The dibromo derivative has shown unexpectedly high reactivity in this reaction, resulting in 4,5-dicarboxamides using primary amines as N-nucleophiles. Monoaminocarbonylation has not been observed, i.e., neither 4-bromo-5-carboxamide nor 4-carboxamido-5-bromo derivatives have been formed. However, the use of secondary amines such as piperidine and morpholine resulted in the formations of mixtures of amino-substituted bromopyridazinones. That is, no carbon monoxide insertion took place in these cases. Some mechanistic details of the formation of aminocarbonylation and amination products are also discussed. |
| |
Keywords: | |
本文献已被 ScienceDirect 等数据库收录! |
|