合成路线:The reduction of 2-nitro-4,5-methylenedioxyacetophenone (I) with H2 over PtO2 in ethanol gives 2-amino-4,5-methylenedioxyacetophenone (II),which is cyclized by treatment with NaNO2 and HCl in water yielding 6,7-methylenedioxycinnolin-4-ol (III).The bromination of (III) with Br2 and potassium acetate in refluxing acetic acid affords 3-bromo-6,7-methylenedioxycinnolin-4-ol (IV),which is treated with Cu2(CN)2 in refluxing DMF giving 4-hydroxy-6,7-methylenedioxycinnolin-3-carbonitrile (V).Alkylation of (V) with ethyl iodide (A) by means of NaH in DMF affords 1-ethyl-6,7-methylenedioxy-4(1H)-oxocinnolin-3-carbonitrile (VI),which is finally hydrolyzed with HCl in refluxing acetic acid.
参考文献标题:Cinoxacin
文献作者:Roberts,P.J.; Castar,J.
参考来源:Drugs Fut 1978,3(1),22
合成路线:The reduction of 2-nitro-4,5-methylenedioxyacetophenone (I) with H2 over PtO2 in ethanol gives 2-amino-4,5-methylenedioxyacetophenone (II),which is cyclized by treatment with NaNO2 and HCl in water yielding 6,7-methylenedioxycinnolin-4-ol (III).The bromination of (III) with Br2 and potassium acetate in refluxing acetic acid affords 3-bromo-6,7-methylenedioxycinnolin-4-ol (IV),which is treated with Cu2(CN)2 in refluxing DMF giving 4-hydroxy-6,7-methylenedioxycinnolin-3-carbonitrile (V).Alkylation of (V) with ethyl iodide (A) by means of NaH in DMF affords 1-ethyl-6,7-methylenedioxy-4(1H)-oxocinnolin-3-carbonitrile (VI),which is finally hydrolyzed with HCl in refluxing acetic acid.
参考文献标题:1-niederalkyl- oder -alkylensubstituierte 6,7-Methylendioxyd-4(1H)-oxocinnolin-3-carbos鋟ren und Zwiswhenprodukte daf黵
文献作者:Maas,I.M.Pfeiffer,W.G.; Voithenleitner,F.
参考来源:DE 2005104; FR 2034519; GB 1296753; GB 1296754
产品链接: CAS No. 28657-80-9››