Homogeneous catalytic aminocarbonylation of nitrogen-containing iodo-heteroaromatics. Synthesis of N-substituted nicotinamide related compounds

Synthesis of Pyridazine Dicarboxamides via Highly Selective Palladium‐catalyzed Aminocarbonylation

“…The 3-carboxamido-6-iodopyridazine intermediate (2′) was identified by MS, however, not isolated ( Table 1, entries 8-10). The high chemoselectivity towards carboxamides obtained in the present reaction can be explained by the similar results published on the aminocarbonylation of 2iodopyridine and iodopyrazine as model substrates [24]. That is, only the insertion of a single carbon monoxide into Pd-aryl bond has led to products when the ring nitrogen of the heteroaromatics is situated in an adjacent position to iodoarene functionality.…”

Chiral heterocyclic ligands. XVII. Pyridine–amino acid hybrid ligands: synthesis and crystal structures of metal complexes of a chelating ligand derived fromL-alanine

“…(1) was prepared by a modification of a reported procedure [11]. The 1 H-and 13 C-NMR spectra were in excellent agreement with literature values [12]. Lithium hydroxide induced hydrolysis of ester 1 produced the free acid 2 as colorless plates in quantitative yield [13].…”

4‐Amino‐TEMPO as N‐Nucleophile in Palladium‐Catalyzed Aminocarbonylation

“…To the best of our knowledge, the N ‐oxyl derivatives have never been used as N ‐nucleophiles in aminocarbonylation to provide an easy access to carboxamides/2‐ketocarboxamides bearing stable radical moiety. Prompted by our previous investigations on the amine screening in the aminocarbonylation of iodoarenes and iodoalkenes , a study on the applicability of 4‐amino‐TEMPO and its analogue without N ‐oxyl functionality in aminocarbonylation was performed.…”