Studies fond of the synthesis of (Z)-5-benzylidene-4-arylpyrrol-2(5H)-ones from (Z)-3-aryl-3-haloenoic acids are

Studies fond of the synthesis of (Z)-5-benzylidene-4-arylpyrrol-2(5H)-ones from (Z)-3-aryl-3-haloenoic acids are described. Hz 2 13 NMR (CDCl3) 187.9 153.9 141 137.8 128.7 127.5 91.8 45 37 21.3 IR (neat) 1639 cm?1; HRMS (ES) m/z calcd for C12H16NO 190.1226 found 190.1168. This compound experienced NMR spectral properties which were consistent with those previously reported.11 4.1 3 (14b) This compound was prepared by the above procedure with the exception that 4-methoxyacetophenone was used in the reaction in which case a 98 % yield of a solid was obtained. This material exhibited the following physical properties: mp 59-63 °C; 1H NMR (CDCl3) 2.99 (broad s 6 3.82 (s 3 5.69 (d 12.6 Hz 1 6.89 (d 7.8 Hz 2 7.76 (d 12.6 Hz 1 and 7.89 (d 8.7 Hz 2 13 NMR (CDCl3) 187.4 161.9 153.8 133.2 129.4 113.3 91.7 55.3 45 37 IR (neat) 1664 cm?1; HRMS (ES) m/z calcd for C12H16NO2 206.1176 found 206.1189. This compound experienced NMR spectral properties which were consistent with those previously reported.11 4.1 1 (14c) This compound was prepared by the above procedure with the exception that 4-chloroacetophenone was used in the reaction in which case a 98 % yield of a solid was obtained. This material exhibited the following physical properties: mp 76-77 °C; 1H NMR Rabbit Polyclonal to APOL1. (CDCl3) 2.57 (broad s 3 2.78 (broad s 3 5.39 (d 12.6 Hz 1 7.09 (d 8.1 Hz 2 7.49 (d 12.6 Hz 2 and 7.60 (d 8.1 Hz 2 13 NMR (CDCl3) 186.2 154.2 138.8 136.4 128.8 128.1 91.3 44.7 37 IR (neat) 1635 cm?1; HRMS (ES) m/z calcd for C11H13ClNO2 210.0680 found 210.0727. This compound experienced NMR spectral properties which were consistent with those previously reported.11 4.1 1 4 (14d) This compound was prepared by the above procedure with the exception that 3 4 was used in the reaction in which case a 98 % yield of a solid was obtained. This material exhibited the following physical properties: mp 112-114 °C; 1H NMR (CDCl3) 2.88 (broad s 6 3.79 (s 3 3.83 WZ4002 (s 3 5.61 (d 12.3 Hz 1 6.75 (d 8.4 Hz 2 7.4 (d 8.4 Hz 2 7.66 (d 12.3 Hz 1 13 NMR (CDCl3) 187.1 153.7 151.5 148.7 133.4 121 110.5 110 91.5 55.9 45 37 IR (neat) 1634 cm?1; HRMS (ES) m/z calcd for C13H18NO3 236.1281 found 236.1300. This compound acquired NMR spectral properties that have been in keeping with those previously reported.12 4.1 WZ4002 (Z)-3-Chloro-3-(p-tolyl)acrylaldehyde (15a) To a circular bottom flask built with a magnetic mix club and reflux condensor was added 3-(dimethylamino)-1-(p-tolyl)prop-2-en-1-one (2.00 g 0.105 mol) phosphorus oxychloride (2 mL 0.021 mol) in 25 mL of dichloromethane. The response mix was refluxed for 2 hours as well as the solvent was WZ4002 taken out The residue was dissolved in 50 ml of the 1:1 WZ4002 combination of drinking water:THF and was permitted to mix at room heat range every day and night. The mix was diluted with drinking water and extracted with ethyl acetate (3 × 30 mL). The organic extract was cleaned with brine (3 × 15 mL) dried out over anhydrous sodium sulfate and focused to produce a dark brown solid (1.87 g 98 % produce). This materials was sufficiently 100 % pure to be utilized in following reactions and exhibited the next physical properties: mp 75-77 °C; 1H NMR (CDCl3) 2.39 (s 3 6.65 (d 6.5 Hz 1 7.26 (d 8 Hz 2 7.65 (d 8 Hz 2 and 10.21 (d 6.5 Hz 1 13 NMR (CDCl3) 191.1 152.2 142.6 132.5 129.5 127.1 123.4 21.3 IR (nice) 1668 cm?1; HRMS (Ha sido) m/z calcd for C10H10ClO 181.0415 found 181.0420. NMR spectral properties were in keeping with those reported previously.13 4.1 (Z)-3-Chloro-3-(4-methoxyphenyl)acrylaldehyde (15c) This substance was made by the above mentioned procedure other than 3-(dimethylamino)-1-(4-methoxyphenyl)prop-2-en-1-one was found in the response in which particular case a 98 % produce of a good was obtained. This materials exhibited the next physical properties: mp 35-37 °C; 1H NMR (CDCl3) 3.88 (s 3 6.63 (d 7 Hz 1 6.98 (d 9 Hz 2 7.75 (d 9 Hz 2 and 10.21 (d 7 Hz 1 13 NMR (CDCl3) 191.5 162.8 152.1 129 127.7 122.6 114.3 and 55.5; IR (nice) 1647 cm?1; WZ4002 HRMS (Ha sido) m/z calcd for C10H10ClO2 197.0364 found 197.0444. NMR spectral properties had been in keeping with those previously reported.10 4.1 (Z)-3-Chloro-3-(4-chlorophenyl)acrylaldehyde (15e) This substance was made by the above mentioned procedure other than 1-(4-chlorophenyl)-3-(dimethylamino)prop-2-en-1-one was found in the response in which particular case a 90 % yield of a solid was obtained. This material exhibited the following physical properties: mp 98-100 °C; 1H NMR (CDCl3) 6.66 (d 6.9 Hz 1 7.46 (d 9.3 Hz 2 7.71 (d 9.3 Hz 2 and 10.23 (d 6.9 Hz 1 13 NMR (CDCl3) 191.5 150.8 138.2 134 129.2 128.4 and 124.6; IR (neat) 1663 cm?1; HRMS (Sera) m/z calcd for.