Synthesis of 2-Chloro-3-Alkyl- And Arylquinolines

Nucleophilic Substitution Reaction of Chloroquinolines With 1,2,4-Triazole. Ii. Synthesis of 2-(1h-1,2,4-Triazol-1-Yl)quinolines

“…Alkyl and methoxy groups at all the positions investigated decrease the reactivity because of their electron-releasing property. Brought to you by | University of California Authenticated Download Date | 6/12/15 6:26 PM Materials: 1H-1,2,4-triazole was purchased from Fluka Chemie AG; 2-chloroquinoline derivatives were prepared according to previously described procedures:la (8), lb (9), lc-p (10,11), It (12), Is (13). For quantitative treatments we investigated the correlation of the reactivity data (log k) at 100 °C for 6-and 7-substituted 2-chloroquinolines with the known (7) Hammett's σ parameters (Figure 2).…”

Selective Palladium‐Catalyzed Aminocarbonylation of Olefins with Aromatic Amines and Nitroarenes

“…(1)]. [17] In summary, we have developed a palladium-based catalyst system for a general and selective aminocarbonylation of olefins with (hetero)aromatic amines to alkanamides. Notably, a wide range of olefins are efficiently transformed to the corresponding N-(hetero)aryl amides in good yields and often with high regioselectivity.…”

“…BINAP, Dppp, L2, and L4) showed low activity in the formation of the desired product ( Table 1, entries [5][6][7][8][9][10][11][12][13][14]. Hence, some of our own developed N-phenylpyrrole-based bisphosphine ligands [14] with different steric properties were tested ( Table 1, entries [15][16][17]. To our delight, L10 was identified as the most promising ligand and the reaction afforded the desired product 3 aa with moderate conversion, albeit with good selectivity.…”

Selective Palladium‐Catalyzed Aminocarbonylation of Olefins with Aromatic Amines and Nitroarenes

“…When monodentate ligands were used, no conversion or just trace amounts of the desired products were observed ( Table 1, entries 1-4). Hence, some of our own developed N-phenylpyrrole-based bisphosphine ligands [14] with different steric properties were tested ( Table 1, entries [15][16][17]. BINAP, Dppp, L2, and L4) showed low activity in the formation of the desired product (Table 1, entries [5][6][7][8][9][10][11][12][13][14].…”

“…[15] Next, p coordination of the olefin to the metal center, followed by insertion into the hydrogen-palladium bond, It should be noted that our new procedure for the preparation of all kinds of N-aryl carboxamides also allows for an efficient synthesis of important heterocycles. [17] In summary, we have developed a palladium-based catalyst system for a general and selective aminocarbonylation of olefins with (hetero)aromatic amines to alkanamides. Indeed, the one-pot synthesis of 6, which has been used as an intermediate for 5hydroxytryptamine antagonists, proceeded smoothly on a gram scale.…”