methyl 2-oxo-1,2,5,6-tetrahydrothieno[2,3-h]quinoline-3-carboxylate -Drug Synthesis Database

【结构式】

【分子编号】56092

【品名】methyl 2-oxo-1,2,5,6-tetrahydrothieno[2,3-h]quinoline-3-carboxylate

【CA登记号】

【分子式】C₁₃H₁₁NO₃S

【分子量】261.30128

【元素组成】C 59.76% H 4.24% N 5.36% O 18.37% S 12.27%

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：(IV)

Enamino ketone (II) was synthesized by treatment of benzothiophenone (I) with dimethylformamide dimethylacetal. Condensation of (II) with methyl cyanoacetate (III) led to the pyridone-fused tricyclic system (IV), which was further aromatized to (V) using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone. Ester group hydrolysis in (V) under acidic conditions afforded acid (VI). This was finally decarboxylated in refluxing quinoline in the presence of copper powder.

参考文献中间体

合成目标

【1】 Fossa, P.; et al.; Novel angular furo and thieno-quinolinones: Synthesis and preliminary photobiological studies. Bioorg Med Chem 2002, 10, 3, 743.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	11045	6,7-Dihydro-1-benzothiophen-4(5H)-one; 4-Keto-4,5,6,7-tetrahydrothianaphthene; Tetrahydrobenzo(b)thiophene-4-one	13414-95-4	C₈H₈OS	详情	详情
(II)	56091	5-[(E)-(dimethylamino)methylidene]-6,7-dihydro-1-benzothiophen-4(5H)-one		C₁₁H₁₃NOS	详情	详情
(III)	34458	Cyanoacetic acid methyl ester; methyl 2-cyanoacetate	105-34-0	C₄H₅NO₂	详情	详情
(IV)	56092	methyl 2-oxo-1,2,5,6-tetrahydrothieno[2,3-h]quinoline-3-carboxylate		C₁₃H₁₁NO₃S	详情	详情
(V)	56093	methyl 2-oxo-1,2-dihydrothieno[2,3-h]quinoline-3-carboxylate		C₁₃H₉NO₃S	详情	详情
(VI)	56094	2-oxo-1,2-dihydrothieno[2,3-h]quinoline-3-carboxylic acid		C₁₂H₇NO₃S	详情	详情

Extended Information