ANTIMALARIALS. α-PHENYL-β-DIALKYLAMINO ALCOHOLS¹

Abstract

This investigation had its beginning in the fall of 1942 as a part of the cooperative effort initiated by the Division of Chemotherapy of the National Institute of Health under Dr. L. F. Small (1) and it was continued into the summer of 1944 at which time, although not completed, it was interrupted because of the greater promise and urgency of other problems. It was based on convincing *

Synthesis of Substituted 1,4-Dioxenes through O–H Insertion and Cyclization Using Keto-Diazo Compounds

“…Purification by flash chromatography (20% Et2O in pentane) afforded alcohol 4c as a white crystalline solid (1.33 g, 82%); R f = 0.27 (20% Et 2 O in pentane); mp = 49−51 °C (lit. 36 mp =59−50 °C (petroleum ether)); IR (film)/cm −1 3412 (br O−H), 2961,2899,1565,1471,1421,1392,1196,1133,1070,1031,993,885,823,743,675,640,581 13 C NMR) were consistent with that previously reported. 32 The reaction was performed on a larger scale (10 mmol acetophenone), which afforded an isolated yield of alcohol (2.28 g, 84%).…”

“…NH 4 Cl (15 mL), brine (15 mL), dried (Na 2 SO 4 ), and concentrated in vacuo. Purification by flash chromatography (20% Et2O in pentane) afforded alcohol 4c as a white crystalline solid (1.33 g, 82%); R f = 0.27 (20% Et 2 O in pentane); mp = 49–51 °C (lit . mp =59–50 °C (petroleum ether)); IR (film)/cm –1 3412 (br O–H), 2961, 2899, 1565, 1471, 1421, 1392, 1196, 1133, 1070, 1031, 993, 885, 823, 743, 675, 640, 581; 1 H NMR (400 MHz, CDCl 3 ) δ7.52 (d, J = 2.0 Hz, 1 H, Ar–H), 7.46 (d, J = 8.3 Hz, 1 H, Ar–H), 7.22 (dd, J = 8.3, 2.0 Hz, 1 H, Ar–H), 4.94–4.86 (m, 1 H, C H (OH)), 3.63 (dd, J = 10.6, 3.4 Hz, 1 H, C H HBr), 3.49 (dd, J = 10.6, 8.6 Hz, 1 H, CH H Br), 2.73 (d, J = 3.1 Hz, 1 H, OH); 13 C­{ 1 H} NMR (101 MHz, CDCl 3 ) δ 140.4 (Ar- C q –CH­(OH)), 132.9 (Ar–C q -Cl), 132.4 (Ar–C q -Cl), 130.6 (Ar–CH), 128.0 (Ar–CH), 125.3 (Ar–CH), 72.5 (CH­(OH)), 39.6 (CH 2 Br).…”

Evaluation of Flavonoid and Resveratrol Chemical Libraries Reveals Abyssinone II as a Promising Antibacterial Lead

“…2‐Bromo‐1‐[4‐(2‐phenylethyl)phenyl]ethanone (13): Column chromatography (silica gel, toluene/hexanes 1:1) afforded the product as a white solid (2153 mg, 71 %); R f =0.20 (toluene/hexanes 1:1); mp: 58–59 °C (lit 45. mp: 61 °C); 1 H NMR (400 MHz, CDCl 3 ): δ =2.91–3.04 (m, 4 H), 4.44 (s, 2 H), 7.13–7.25 (m, 3 H), 7.26–7.32 (m, 4 H), 7.90 ppm (d, J =8.4 Hz, 2 H); 13 C NMR (100 MHz, CDCl 3 ): δ =31.0, 37.4, 38.0, 126.3, 128.6, 129.2, 129.3, 132.1, 141.1, 148.7, 191.1 ppm; HRMS‐EI m / z [ M ] + calcd for C 16 H 15 BrO: 302.0306, found: 302.0301.…”

Efficient Synthetic Approach to Substituted Benzo[b]furans and Benzo[b]thiophenes by Iodine‐Promoted Cyclization of Enaminones

“…Compounds 5a , 5b , 5c , 5d , 5e and 5g , 5h , 5i , 5j , as well as enaminones 3a , 3b , 3c , 3d , 3e and 3g , 3h , 3i , 3j , were prepared as reported. 2‐Bromoacetophenones 9e , 9f , 9g , 9h , 9i , 9j and 1‐(3‐bromo‐4‐methoxyphenyl)ethanone ( 10f ) were synthesized, and their spectroscopic data were compared with those previously described.…”