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Synthesis of Pyridazine Dicarboxamides via Highly Selective Palladium‐catalyzed Aminocarbonylation
Author(s) -
Szőke Gyöngyi,
Takács Attila,
Kollár László
Publication year - 2016
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.2523
Subject(s) - chemistry , pyridazine , palladium , carbon monoxide , substituent , carbonylation , catalysis , selectivity , ring (chemistry) , combinatorial chemistry , medicinal chemistry , primary (astronomy) , organic chemistry , physics , astronomy
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.