新产品编号:280523
Chemical Name: trans-3-Propyl-5,6,6a,7,8,12b-hexahydronaphtho[1,2-f][1,7]naphthyridine-10,11-diol
CAS No. 197007-99-1, 197007-53-7 (diHBr)
项目整合开发状态: Biological Testing
项目研究机构: Abbott (Originator)
合成路线:6-Propyl-2-pyridinecarboxylic acid (I) was activated as the mixed anhydride with pivaloyl chloride,and then condensed with tert-butylamine to afford amide (II).After treatment of (II) with butyllithium,the resulting dianion equilibrated to the trans isomer upon treatment with Et3N in MeOH.Reduction of (IV) with concomitant cyclization in the presence of Zn and HCl furnished the tetracyclic compound (V).Finally,cleavage of the methyl ethers of (V) using BBr3 yielded the was condensed with nitroolefin (III) to provide a cis/trans mixture of adducts (VI),which was target compound.
📌 参考资料/链接：
参考文献标题:Trans-2,6-,3,6- and 4,6-diaza-5,6,6a,7,8,12b-hexahydrobenzo[c]phenanthrene cpds.as dopamine agonists
文献作者:Michaelides,M.; Gu,Y.G.; Shiosaki,K.(Abbott Laboratories Inc.)
参考来源:US 5668141; WO 9736902
📄 详细内容
合成路线:6-Propyl-2-pyridinecarboxylic acid (I) was activated as the mixed anhydride with pivaloyl chloride,and then condensed with tert-butylamine to afford amide (II).After treatment of (II) with butyllithium,the resulting dianion equilibrated to the trans isomer upon treatment with Et3N in MeOH.Reduction of (IV) with concomitant cyclization in the presence of Zn and HCl furnished the tetracyclic compound (V).Finally,cleavage of the methyl ethers of (V) using BBr3 yielded the was condensed with nitroolefin (III) to provide a cis/trans mixture of adducts (VI),which was target compound.
参考文献标题:trans-2,6-,3,6- and 4,6-diaza-5,6,6a,7,8,12b-hexahydro-benzo[c]phenanthrene-10,11-diols as dopamine agonists
文献作者:Gu,Y.G.; Bayburt,E.K.; Michaelides,M.R.; Lin,C.W.; Shiosaki,K.
参考来源:Bioorg Med Chem Lett 1999,9(10),1341