Amination of aryl halides using copper catalysis

Synthesis and Antimalarial Properties of New Chloro‐9H‐xanthones with an Aminoalkyl Side Chain

“…13 C-NMR (75 MHz, CDCl 3 ): 178.8 (C(9)); 158.0 (C(10a)); 155.5 (C(4a)); 151.8 (C(1)); 139.9 (C(6)); 136.2 (C(3)); 127.5 (C(8)); 124.1 (C(7)); 120.8 (C(8a)); 117.2 (C(5)); 106.7 (C(9a)); 104.1 (C(2)); 102.0 (C(4)); 51.3 (C(2')); 47.2 (C(3')); 41.4 (C(1')); 11.8 (C(4') (2)); 3.34 (q, J ¼ 6.4, CH 2 (1')); 2.80 (t, J ¼ 6.8, CH 2 (2')); 2.64 (q, J ¼ 7.1, CH 2 (3')); 1.09 (t, J ¼ 7.1, Me(4')). [58]. Two strains of Plasmodium falciparum were used, 3D7 (susceptible to chloroquine) and Dd2 (resistant to chloroquine).…”

“…The new compounds 1 and chloroquine (pos. control) [58] were dissolved in culture medium and passed through sterile filters (0.22 mm). The micro-plates were titrated with two-fold serial dilutions of each compound as well as the control.…”

“…Herein, we describe the synthesis of compounds 1a -1l by Ullmann-type ether condensation [55] [56], intramolecular Friedel -Crafts acylation [57], and Cu-catalyzed N-arylation [58] as key steps. We also report the toxic action of these new compounds towards the malarial parasite using the WHO Mark-III test [59] for two different strains of P. falciparum, i.e., the 3D7 and the Dd2 strains, which are susceptible and resistant, respectively, to chloroquine, mefloquine, and quinine.…”

“…Finally, the substituted amino group in position 1 was introduced by heating 8 with 4 equiv. of N,Ndiethylethane-1,2-diamine (9) in MeOH and in the presence of Cu 2 O as catalyst [58]. Compounds 1j -1l (Scheme 2) were prepared via compounds 10 -17 in analogy as described above, but using methyl 2,6-dichlorobenzoate (12) as the ester component to guarantee a Cl-atom in position 1 of the xanthone 17.…”

Direct Synthesis of Secondary Amines From Alcohols and Ammonia Catalyzed by a Ruthenium Pincer Complex

“…Because of the abundance and low price of ammonia, much attention has been focused on its use as a nitrogen source for organic synthesis [4,5]. Recent reports on homogenous catalytic systems using ammonia as the substrate include palladium-catalyzed telomerization of butadiene and ammonia giving primary alkylamines [6], Pd-catalyzed allylic amination [7], copper-and palladiumcatalyzed coupling reactions of ammonia with aryl halides to form arylamines [8][9][10], rhodium-and iridium-catalyzed reductive aminations of carbonyl compounds with ammonium formate and ammonia to afford primary alkylamines [11][12][13] and palladium-catalyzed arylation of ammonia to afford di-and triarylamines [10].…”