【结 构 式】 |
【分子编号】30690 【品名】isopropyl isocyanate; 2-isocyanatopropane 【CA登记号】1795-48-8 |
【 分 子 式 】C4H7NO 【 分 子 量 】85.10572 【元素组成】C 56.45% H 8.29% N 16.46% O 18.8% |
合成路线1
该中间体在本合成路线中的序号:(II)1) By condensation of 3-sulfonamido-4-(3-methylanilino)pyridine (I) with isopropylisocyanate (II) by means of triethylamine at 95 C.
【1】 Delarge, J.E.; Lapiere, C.L.; Georges, A.M. (A. Christiaens SA); 3-Loweralkylcarbamylsulfonamido-4-phenylaminopyridine-N-oxides, derivatives thereof and pharmaceutical compositions containing same. BE 0827844; CH 609045; CH 610890; DD 121936; DD 126887; DE 2516025; FR 2267775; GB 1477664; JP 50142571; NL 7504521; US 4018929; US 4055650; ZA 7502243 . |
【2】 Castaner, J.; Blancafort, P.; Thorpe, P.; Serradell, M.N.; Torasemide. Drugs Fut 1983, 8, 3, 223. |
合成路线2
该中间体在本合成路线中的序号:The hetero Diels-Alder condensation of quinolinedione (I) with the azabutadiene (II) in the presence of ZnBr2 produced regioselectively the pyridoquinoline (III). Benzylic bromination of (III) using N-bromosuccinimide then gave bromomethyl derivative (IV). Subsequent treatment of (IV) with NaOAc in DMF, followed by hydrolysis of the resulting acetate (V), afforded 3-(hydroxymethyl)pyridoquinoline (VI). This was finally treated with isopropyl isocyanate in the presence of Et3N and dibutyltin diacetate to yield the target carbamate.
【1】 Lee, H.; Lee, S.I.; Yang, S.I.; Synthesis and in vitro cytotoxicity of 3-substituted-1,8-diazaanthraquinones produced by Lewis-acid catalyzed hetero Diels-Alder reaction. Bioorg Med Chem Lett 1998, 8, 21, 2991. |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
30690 | isopropyl isocyanate; 2-isocyanatopropane | 1795-48-8 | C4H7NO | 详情 | 详情 | |
(I) | 25759 | 5,8-quinolinedione | C9H5NO2 | 详情 | 详情 | |
(II) | 25760 | 2-methylacrylaldehyde N,N-dimethylhydrazone | C6H12N2 | 详情 | 详情 | |
(III) | 25761 | 3-methylpyrido[3,2-g]quinoline-5,10-dione | C13H8N2O2 | 详情 | 详情 | |
(IV) | 25762 | 3-(bromomethyl)pyrido[3,2-g]quinoline-5,10-dione | C13H7BrN2O2 | 详情 | 详情 | |
(V) | 25763 | (5,10-dioxo-5,10-dihydropyrido[3,2-g]quinolin-3-yl)methyl acetate | C15H10N2O4 | 详情 | 详情 | |
(VI) | 25764 | 3-(hydroxymethyl)pyrido[3,2-g]quinoline-5,10-dione | C13H8N2O3 | 详情 | 详情 |