New complexes constructed based on (1H-tetrazol-5-yl)phenol: Synthesis, structures and properties

Azole-Based Indoleamine 2,3-Dioxygenase 1 (IDO1) Inhibitors

“…Compounds 4a–4f have been described previously by us . Other compounds were synthesized according to literature procedures [( 1b , 1c , 1e ), ( 1d , 1f ), , ( 2a–f ), − ( 3c , 3e ), , ( 3f ), ( 5b–c , 5e–g ), ( 6c , 6e–f ), 9 , 15 , 17 , 20 , 21 , and 23 ] . Briefly, the 4-phenylimidazole derivatives 1b – c and 1e were obtained by the reaction of α-bromoketone derivatives ( 36b–c , 36e ) with formamide (Scheme ).…”

“…Compounds 4a−4f have been described previously by us. 50 Other compounds were synthesized according to literature procedures [(1b, 1c, 1e), 20 (1d, 1f), 20,59 (2a−f), 59−61 (3c, 3e), 61,62 (3f), 62 (5b−c, 5e−g), 63 (6c, 6e−f), 64 9, 65 Aryl iodide 39f reacted with imidazole in the presence of N,N′dimethylethylenediamine, Cs 2 CO 3 , and CuI in DMF at 140 °C to produce 3f. In the same way, the aryl methyl ethers 40 and 41 were converted to the corresponding N-aryl imidazoles, followed by demethylation with 48% HBr in H 2 O at 100 °C to produce phenols 3c and 3e, respectively (Scheme 3).…”

“…2-(1 H -Tetrazol-5-yl)­phenol ( 6c ) . Synthesized from 2-hydroxybenzonitrile ( 45c ) and NaN 3 according to the general procedure to afford 6c as a white solid in 80% yield.…”

“…General Procedure for the Synthesis of 1,2,3,4-Tetrazoles (6c, 6e, and 6f). 64 A mixture of the corresponding carbonitrile (45c,e,f) (1 mmol, 1 equiv), NaN 3 (2 mmol, 3 equiv), and Et 3 N•HCl (3.7 mmol, 3.7 equiv) in toluene (3 mL) was stirred at 99 °C overnight. After cooling to r.t., the mixture was extracted with H 2 O (2 mL) and the aqueous phase was acidified by dropwise addition of conc.…”

“…2-(1H-Tetrazol-5-yl)phenol (6c). 64 Synthesized from 2-hydroxybenzonitrile (45c) and NaN 3 according to the general procedure to afford 6c as a white solid in 80% yield. 1 H NMR (400 MHz, CD 3 OD): δ 8.08 (dd, J = 7.8, 1.7 Hz, 1H), 7.44 (ddd, J = 8.3, 7.3, 1.7 Hz, 1H), 7.10−7.02 (m, 2H), 13 C NMR (100 MHz, CD 3 OD): δ 155.…”