Phenacyl bromide: A versatile organic intermediate for the synthesis of heterocyclic compounds

Recent advances in the transition-metal-free synthesis of quinoxalines

“…Owing to the dual functionality as they contain two electrophilic sites, α-halo-ketones are recently gained as important building blocks for the synthesis of numerous active heterocycles as well as undergo various types of reaction. 76 α-Halo-ketones mainly phenacyl bromides were utilized in the synthesis of quinoxaline derivatives.…”

Metal-Free Indole–Phenacyl Bromide Cyclization: A Regioselective Synthesis of 3,5-Diarylcarbazoles

“…2,4-Bis-biphenyl-4-yl-6-methoxy-9H-carbazole (3c): brown solid (10% ethyl acetate/petroleum ether); 70% (350 mg, 0.70 mmol); mp 186−188 °C; 1 H NMR (CDCl 3 , 300 MHz) δ 3.66 (s, 3H), 7.03−7.06 (m, 1H), 7.11 (d, 1H, J = 2.1 Hz), 7.34 (d,1H,J = 8.4 Hz),7.38 (s,1H),7.42 (d,1H,J = 3.3 Hz),5H),7H), 7.82 (d, 6H, J = 10.2 Hz), 8.12 (brs, 1H); 13 C{ 1 H} NMR (CDCl 3 ,75 MHz) δ 55. 6, 105.5, 108.0, 111.0, 114.9, 120.2, 123.2, 127.0, 127.1, 127.3, 127.4, 127.5, 127.8, 128.8, 128.9, 129.8, 135.1, 137.4, 138.4, 140.0, 140.4, 140.5, 140.7, 140.9, 141.3, 153.4; FT-IR (KBr, cm −1 ) 752, 831,1230,1323,1456,2853,2924,2973,3395,3416; HRMS (ESI) (m/z) [M + H] + calcd for C 37 H 28 NO 502.2171, found 502.2169.…”

“…2,4-Di-p-tolyl-9H-carbazole (3d): brown solid (6% ethyl acetate/ petroleum ether); 72% (250 mg, 0.72 mmol); mp 152−154 °C; 1 H NMR (CDCl 3 , 300 MHz) δ 2.43 (s. 3H), 2.52 (s, 3H), 7.00−7.05 (m, 1H), 7.29 (d,2H,J = 8.7 Hz),5H),6H),8.19 (brs,1H); 13 C{ 1 H} NMR (CDCl 3 ,75 MHz) δ 21. 0, 21.2, 107.4, 110.2, 119.0, 119.8, 120.6, 122.3, 122.8, 125.4, 127.2, 129.0, 129.0, 129.4, 136.8, 137.1, 137.8, 138.2, 138.6, 138.9, 140.0, 140.4; FT-IR (KBr, cm −1 ) 736,1282,1323,1455,1513,1605,2852,2920,3022,3050,3440; HRMS (ESI) (m/z) [M + Na] + calcd for C 26 H 21 NNa 370.1572, found 370.1574.…”

Synthetic Access to Aromatic α-Haloketones

“…Therefore, the present contribution aims to describe and evaluate the diverse protocols leading to α-haloketones that have been published over the past two decades. Since the number of reports in the literature is quite significant, this review will be limited to methods generating carbonyl compounds carrying one halogen atom at their α-position, and will mainly focus on aromatic α-haloketones compounds, as these appear to have the highest synthetic value [ 34 , 35 , 36 ].…”