合成路线:This compound can be obtained in the following way:1) The reaction of N,N-dimethyl 4-methoxybenzamide (I) with 2-(methylthio)pyrrole) (II) by means of POCl3 in refluxing dichloromethane gives 5-(4-methoxyhenzoyl)-2-(methylthio)pyrrole (III),which is oxidized with m-chloroperbenzoic acid in dichloromethane to the corresponding sulfone (IV).The condensation of (IV) with 5,5-dimethylene-2,2-dimethyl-1,3-dioxane-4,6-dione (V) by means of NaH in hot DMF affords the intermediate compound (VI),which by methanolysis with methanol and HCl is converted to 5-(4 methoxybenzoy)-1-[3,3-di-(methoxycarbonyl)propyl]-2-(methylsulfonyl)pyrrole (VII).The cyclization of (VII) by means of NaH in hot DMF gives dimethyl-5-(4-methoxybenzoyl)-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1,1-dicarboxylate (VIII),which is finally hydrolyzed and decarboxylated with KOH in refluxing methanol-water.
参考文献标题:Process for preparing 5-aroyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acids and novel intermediates therein
文献作者:Muchowski,J.M.; Greenhouse,R.(Roche Bioscience)
参考来源:US 4347186
合成路线:This compound can be obtained in the following way:1) The reaction of N,N-dimethyl 4-methoxybenzamide (I) with 2-(methylthio)pyrrole) (II) by means of POCl3 in refluxing dichloromethane gives 5-(4-methoxyhenzoyl)-2-(methylthio)pyrrole (III),which is oxidized with m-chloroperbenzoic acid in dichloromethane to the corresponding sulfone (IV).The condensation of (IV) with 5,5-dimethylene-2,2-dimethyl-1,3-dioxane-4,6-dione (V) by means of NaH in hot DMF affords the intermediate compound (VI),which by methanolysis with methanol and HCl is converted to 5-(4 methoxybenzoy)-1-[3,3-di-(methoxycarbonyl)propyl]-2-(methylsulfonyl)pyrrole (VII).The cyclization of (VII) by means of NaH in hot DMF gives dimethyl-5-(4-methoxybenzoyl)-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1,1-dicarboxylate (VIII),which is finally hydrolyzed and decarboxylated with KOH in refluxing methanol-water.
参考文献标题:Anirolac
文献作者:Prous,J.; Castar,J.
参考来源:Drugs Fut 1986,11(6),449
合成路线:This compound can be obtained in the following way:1) The reaction of N,N-dimethyl 4-methoxybenzamide (I) with 2-(methylthio)pyrrole) (II) by means of POCl3 in refluxing dichloromethane gives 5-(4-methoxyhenzoyl)-2-(methylthio)pyrrole (III),which is oxidized with m-chloroperbenzoic acid in dichloromethane to the corresponding sulfone (IV).The condensation of (IV) with 5,5-dimethylene-2,2-dimethyl-1,3-dioxane-4,6-dione (V) by means of NaH in hot DMF affords the intermediate compound (VI),which by methanolysis with methanol and HCl is converted to 5-(4 methoxybenzoy)-1-[3,3-di-(methoxycarbonyl)propyl]-2-(methylsulfonyl)pyrrole (VII).The cyclization of (VII) by means of NaH in hot DMF gives dimethyl-5-(4-methoxybenzoyl)-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1,1-dicarboxylate (VIII),which is finally hydrolyzed and decarboxylated with KOH in refluxing methanol-water.
参考文献标题:Novel syntheses of 5-aroyl-1,2-dihydro-3H-pyrrole-1-carboxilic acids
文献作者:Greenhouse,R.; Franco,F.
参考来源:J Org Chem 1982,471682
产品链接: CAS No. 66635-85-6››