One‐Step Synthesis of Dicarboxamides through Pd‐Catalysed Aminocarbonylation with Diamines as N‐Nucleophiles

Abstract

An efficient one-step synthetic strategy was used to prepare a set of dicarboxamides through palladium-catalysed aminocarbonylation of iodoalkenyl and iodoaryl compounds, with use of various alkyl-and aryldiamines as N-nucleophiles. The isolated yields of the dicarboxamides depended significantly on the iodo substrate and diamine structures, as well as on the reaction conditions, the best one (ca. 70 %) being achieved with 1-iodocyclohexene as substrate and 1,4-diaminobutane as nucleophile, at 100°C and 30 bar of CO.

A New Tool in the Quest for Biocompatible Phthalocyanines: Palladium Catalyzed Aminocarbonylation for Amide Substituted Phthalonitriles and Illustrative Phthalocyanines Thereof

“…According to previously described [49,51,[61][62][63][64], a simplified mechanism for the formation of 4amide substituted phthalonitrile is proposed in Figure 1 All carboxamide substituted phthalonitriles were characterized by 1 H, 13 C-NMR and mass spectrometry and their structures confirmed. It is worth mentioning that, under the reaction conditions employed (100 °C and 5 bar), 100% chemoselectivity toward the mono-carboxamide products was obtained, since no double carbon monoxide insertion product was observed, using these amines as nucleophiles [55,65]. Using similar conditions, we also investigated the use of cyclic diamines in the palladium catalyzed aminocarbonylation reaction for the synthesis of N-mono-substituted diamines.…”

Modellvegyületektől a gyakorlati fontosságú származékokig: barangolásaim a szervetlen és szerves kémia határterületein

“…Ábra A 11-karbonsavamidok szintézisét modellvegyületekkel is megvalósítottuk. Androszt-4-én-3,11,17-trion (adrenoszteron) 3-és 17-keto-csoportját (itt nem részletezett) standard reakciókkal redukáltuk, majd a 11-on csoportból kialakított 11-jód-11-én aminokarbonilezésével a megfelelõ karbonsavamidot nyertük 34,35 (38. Ábra).…”

Synthesis of Aromatic Amide Derivatives and Their Biological Evaluation against Protein Tyrosine Phosphatase 1B and Scr Homology-2 Domain Containing Protein Tyrosine Phosphatase-2

“…目标化合物在 20 μg/mL 的浓度下, 对 PTP1B 和 SHP2 进行初筛, 将抑制率高于 50%的化合物进行复筛, [16] : 灰白色固体, [18] [19] N,N'-二苯基对苯二甲酰胺(6a) [20] [24] : 灰白色固 …”