Substituted azole five-membered heterocyclic derivatives and their solvothermal one-pot synthesis and application
A kind of technology of five-membered heterocycle and derivatives, applied in the field of organic synthesis
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Embodiment 1
[0062] The synthesis of embodiment 1,2,5 diphenyloxazole ((II) 1)
[0063]
[0064] Add 25mL of pyridine, 2.39g of N-(2-oxo-2-phenyl)ethylbenzamide and 1.7g of phosphorus pentoxide into a 100mL reaction kettle, mix well, tighten the sealing cap, and put it into an electric blast drying oven In the process, heat up from room temperature to a reaction temperature of 120°C. After constant temperature reaction for 6 hours, stop heating and cool down to room temperature naturally. The mixture is washed with distilled water, dried, recrystallized from ethanol, and weighed to obtain 1.82 g of a light yellow solid (II). 1. The yield is 82.3%.mp: 180.1~183.6℃.IRν(cm -1 ):3045,1584,1483,1443,1126,1062,1020,944,908,820,760,683; 1 H-NMR (CDCl 3 ,400MHz):8.12(dd,J=7.7,1.5Hz,2H),7.74(dd,J=8.2,1.3Hz,2H),7.51–7.44(m,6H),7.35(t,J=7.5Hz, 1H); 13 C-NMR (125MHz, CDCl 3 ): 161.5, 151.7, 130.8, 129.4, 129.3, 128.9, 128.4, 127.9, 126.7, 124.6, 123.9; HRMS (MALDI-FTMS) calcd for C 15 h 12 N...
Embodiment 2
[0065] The synthesis of embodiment 2,2-indolyl-5-phenyloxazole ((II) 2)
[0066]
[0067] Add 25mL of toluene, 2.78g of N-(2-oxo-2-phenyl)ethyl-1H-indole-3-carboxamide and 1.7g of phosphorus pentoxide into a 100mL reactor, mix well, and tighten the sealing cap. Put it into an electric blast drying box, heat up from room temperature to a reaction temperature of 150°C, and after constant temperature reaction for 6 hours, stop heating and cool down to room temperature naturally, wash the mixture with distilled water, dry, recrystallize with ethanol, weigh, and obtain light White solid 2.31g (Ⅱ) 2, yield rate is 88.7%.IRν(cm -1 ):3413,3154,2919,1625,1602,1443,1361,1249,1120,914,767,726; 1 H-NMR (400MHz, DMSO-d 6 ):8.10–8.07(m,2H),7.98–7.95(m,2H),7.60–7.48(m,5H),7.25–7.17(m,2H); 13 C-NMR (125MHz, DMSO-d 6 ):158.0, 148.3, 136.4, 130.1, 129.2, 127.2, 125.5, 123.9, 123.5, 122.3, 120.8, 120.3, 119.6, 112.2, 103.6; HRMS (MALDI-FTMS) calcd for C 17 h 13 N2O + [M+H] + 261.1022,...
Embodiment 3
[0068] The synthesis of embodiment 3,2-indolyl-5 pyridyl oxazole ((II) 3)
[0069]
[0070] Add 25mL of xylene, 2.78g of N-(2-oxo-2-pyridyl)ethyl-1H-indole-3-carboxamide and 1.7g of phosphorus pentoxide into a 100mL reactor, mix well, and tighten the sealing cap , put it into an electric blast drying oven, heat up from room temperature to a reaction temperature of 150°C, and after constant temperature reaction for 6 hours, stop heating and cool down to room temperature naturally, wash the mixture with distilled water, dry, recrystallize with ethanol, and weigh to obtain Yellow solid 2.35g (Ⅱ) 3, the yield is 90%.IRν(cm -1 ):3173,2919,1755,1628,1431,1331,1255,1120,1008,920,803,750,703,614; 1 H-NMR (400MHz, DMSO-d 6 ):9.27(s,1H),8.69(d,J=5.0Hz,1H),8.41(d,J=6.7Hz,1H),8.01(d,J=2.4Hz,1H),7.97(d,J =7.9Hz,1H),7.67(s,1H),7.59(dd,J=7.9,5.0Hz,1H),7.49(d,J=7.9Hz,1H),7.25–7.17(m,2H); 13 C-NMR (100MHz, DMSO-d 6 ):155.9, 150.6, 149.0, 136.4, 132.8, 124.2, 124.1, 123.5, 123.4, 122.3,...
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