MS-857

合成路线:This compound can be prepared by several different ways:1) The reaction ot 4-(chloromethyl)pyridine (I) with NaCN in toluene - water gives 4-(cyanomethyl)pyridine (II),which is condensed with methyl acrylate (III) yielding dimethyl 4-cyano 4-(4-pyridyl)pimelate (IV).The hydrolysis and decarboxylation of (IV) atfords 4-(4-pyridyl)pimelic acid (V),which is cyclized by means of potassium tert-butoxide giving 4-(4-pyridyl)cyclohexanone (VI).The acetylation of (VI) with acetic anhydride or acetylimidazole affords 2-acetyl(4-4 pyridyl)cyclohexanone (VII),which is finally cyclized with acetylacetamide (VIII) by means of dimethylamine.2) The cyclization of (VII) with cyanoacetamide (IX) by means of piperidine gives 4-cyano-1-methyl-7-(4-pyridyl)-5,6,7,8-tetrahydro-3(2H)-isoquinolinone (X),which is finally treated with methyl magnesium iodide in ether.3) The condensation of 4 bromopyridine (XI) and cyclohexanedione monoethyleneketal (XII) by means of butyllithium in THF gives 4-hydroxy-4-(4-pyridyil)cyclohexanone ethyleneketal (XIII),which is dehydrated by treatment with SOCl2 and then with NaOH to afford 4-(4-pyridyl)-3-cyclohexenone ethyleneketal (XIV).Finally,this compound is hydrolyzed with HCl and reduced with H2 over Pd/C in 0.5 N HCl yielding cyclohexanone (VII),already obtained.

参考文献标题:Process for preparing 4-acetyl isoquinolinone cpds
文献作者:Fukazawa,N.; Kaiho,T.; Yamashita,H.(Mitsui Chemicals,Inc.)
参考来源:JP 1987187467; US 4814458


合成路线:This compound can be prepared by several different ways:1) The reaction ot 4-(chloromethyl)pyridine (I) with NaCN in toluene - water gives 4-(cyanomethyl)pyridine (II),which is condensed with methyl acrylate (III) yielding dimethyl 4-cyano 4-(4-pyridyl)pimelate (IV).The hydrolysis and decarboxylation of (IV) atfords 4-(4-pyridyl)pimelic acid (V),which is cyclized by means of potassium tert-butoxide giving 4-(4-pyridyl)cyclohexanone (VI).The acetylation of (VI) with acetic anhydride or acetylimidazole affords 2-acetyl(4-4 pyridyl)cyclohexanone (VII),which is finally cyclized with acetylacetamide (VIII) by means of dimethylamine.2) The cyclization of (VII) with cyanoacetamide (IX) by means of piperidine gives 4-cyano-1-methyl-7-(4-pyridyl)-5,6,7,8-tetrahydro-3(2H)-isoquinolinone (X),which is finally treated with methyl magnesium iodide in ether.3) The condensation of 4 bromopyridine (XI) and cyclohexanedione monoethyleneketal (XII) by means of butyllithium in THF gives 4-hydroxy-4-(4-pyridyil)cyclohexanone ethyleneketal (XIII),which is dehydrated by treatment with SOCl2 and then with NaOH to afford 4-(4-pyridyl)-3-cyclohexenone ethyleneketal (XIV).Finally,this compound is hydrolyzed with HCl and reduced with H2 over Pd/C in 0.5 N HCl yielding cyclohexanone (VII),already obtained.
参考文献标题:MS-857
文献作者:Prous,J.; Castar,J.
参考来源:Drugs Fut 1988,13(9),831


产品链接: CAS No. 107189-96-8››