3-methylpyrido[3,2-g]quinoline-5,10-dione -Drug Synthesis Database

【结构式】

【分子编号】25761

【品名】3-methylpyrido[3,2-g]quinoline-5,10-dione

【CA登记号】

【分子式】C₁₃H₈N₂O₂

【分子量】224.2188

【元素组成】C 69.64% H 3.6% N 12.49% O 14.27%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(III)

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.

参考文献中间体

合成目标

【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

Extended Information