Synthetic Route of 5428-09-1,Some common heterocyclic compound, 5428-09-1, name is 2-Allylisoindoline-1,3-dione, molecular formula is C11H9NO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
Following a slightly modified procedure,3 14 (222 mg, 1.0 mmol, 1.0 equiv) was dissolved in 1 mL of ethylacetate to obtain a 1 M solution. The solution was warmed up to 80 °C with 2-allylisoindoline-1,3-dione(374 mg, 2.0 mmol, 2.0 equiv). After 15 minutes of reflux under nitrogen, DLP (40 mg, 0.1 mmol, 0.1equiv) was added and the solution was stirred 1 hour and monitored by TLC. The crude was concentratedin vacuo and purified by flash column chromatography (PE:EtOAc 80:20 to 70:30) to afford pure 26 (370mg, 0.9 mmol, 90percent) as a light yellow oil and as a mixture of diastereoisomers. Rf (PE:EtOAc 8:2) = 0.12.1H NMR (CDCl3, 400 MHz) delta 7.84-7.80 (m, 2 H, ArH), 7.73?7.69 (m, 2 H, ArH), 4.60-4.49 (m, 2 H,OCH2CH3), 4.27-4.15 (m, 1 H, CHS), 4.03-3.88 (m, 2 H, CH2N), 3.35-3.20 (m, 2 H, CH2S), 2.78-2.64 (m,1.5 H, CH2CH2S, CHCOS), 2.60-2.54 (m, 1 H, CH2CH2S), 2.28-2.18 (m, 1 H, CHCH2CH), 2.05-1.95 (m,0.5 H, CH2CHS), 1.92-1.81 (m, 0.5 H, CH2CH2S), 1.75-1.65 (m, 1 H, CHCH2CH), 1.38 (t, 1.5 H, J = 7.1Hz, OCH2CH3), 1.37 (t, 1.5 H, J = 7.1 Hz, OCH2CH3). 13C NMR (CDCl3, 101 MHz) delta 212.5 (CS2), 212.3(CS2), 209.3 (COS), 209.2 (COS), 168.1 (N(CO)2), 134.2 (ArH), 131.7 (Ar), 123.5 (ArH), 70.6 (OCH2CH3),70.4 (OCH2CH3), 49.5 (CHCOS), 48.3 (CHS), 41.8 (CH2N), 40.3 (CH2N), 32.7 (CH2CH2S), 32.4(CH2CH2S), 32.1 (CHCH2CH), 31.8 (CHCH2CH), 30.3 (CH2CH2S), 30.2 (CH2CH2S), 13.7 (OCH2CH3).COSY, HSQC and HMBC were consistent with this attribution. IR 1773 (NC=O), 1718 (SC=O, NC=O),1223 (SC-O), 1048 (C=S). HRMS (EI) calculated for C18H19NO4S3 [M+] 409.0476; found 409.0481, fragmentationcalculated for C15H14NO3S [M+] 288.0694; found 288.0689.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Allylisoindoline-1,3-dione, its application will become more common.