Electric Literature of 43088-72-8,Some common heterocyclic compound, 43088-72-8, name is 6-Methoxyisochroman-3-one, molecular formula is C10H10O3, 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.
General procedure: A mixture of 6-methoxyisochroman-3-one 3242 (300 mg, 1.68 mmol), amine analogues (a – g) (2.52 mmol) and AlCl3 (45.0 mg, 0.340 mmol) were combined under anhydrous conditions in a sealed tube and heated at 150 oC for 48 h. The reaction mixture was poured into aqueous 1 N HCl (5.0 mL) and extracted with EtOAc (20 mL x 2) to afford a brown residue which was purified with column chromatography (30:70 EtOAc/Hexane). 6-Methoxy-2-(4?-methylthiazol-2-yl)-1,2-dihydroisoquinolin-3(4H)-one (33a) was obtained from 32 as a pale yellow residue (162 mg, 35%), Rf 0.76 (50:50 EtOAc/Hexane). 1H NMR (300 MHz, CDCl3): deltaH 7.27-7.25 (m, 1H, ArH), 6.84-6.75 (m, 2H, ArH), 6.58 (s, 1H, thiazole-H), 5.29 (s, 2H, ArCH2N), 3.83-3.80 (m, 5H, overlapping signals-OMe and CH2), 2.33 (s, 3H, thiazole-Me). 13C NMR (75 MHz, CDCl3): deltaC 17.7 (thiazole-Me), 39.1 (ArCH2), 49.7 (ArCH2N), 55.7 (OMe), 110.0 (thiazole-CH), 112.5 (ArCH), 113.3 (ArCH), 123.7(ArCH), 127.4 (ArC), 132.8 (ArC), 147.0 (thiazole-CMe), 158.7 (thiazole-ArCN), 159.8 (C-O), 168.4 (C=O). HRMS ESI+ calcd for C14H15N2O2S [M+H]+, 275.0854, found, 275.0855.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Methoxyisochroman-3-one, its application will become more common.
Reference:
Article; Mabank, Tanya; Alexandre, Kabamba B.; Pelly, Stephen C.; Green, Ivan R.; van Otterlo, Willem A.L.; Arkivoc; vol. 2019; 4; (2019);,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics