【药物名称】OROS(R)-tacrine, Tacrine hydrochloride, CI-970, THA.HCl, Cognex
化学结构式(Chemical Structure):
参考文献No.12017
标题:7,8,9,10-Tetrahalo-6H-cyclohepta[b]quinolines
作者:Sigal, M.V. Jr.; Brent, B.J.; Marchini, P.
来源:US 3232945
合成路线图解说明:

The cyclocondensation of aniline (VII) with ethyl 2-oxocyclo-hexanecarboxylate (VIII) by means of HCl in refluxing benzene gives 9-acridone (IX), which by treatment with refluxing POCl3 is converted to 9-chloroacridine (X). Finally, this compound is treated with anhydrous NH3 in p-cresol), or with ethanolic ammonia with a Cu catalyst.

合成路线图解说明:

This compound can be prepared by two different methods: 1) By cyclocondensation of p-anisidine (I) with 2-oxocyclohexanecarboxylate (II) to 7-methoxy-1,2,3,4-tetrahydroacridone (III), which by treatment with refluxing POCl3 is converted to 9-chloro-7-methoxy-1,2,3,4-tetrahydroacridine (IV). This compound is converted to final product by treatment with NH3 in refluxing p-cresol. 2) By cyclocondensation of 5-methoxyisatin (V) and cyclohexanone (VI) in concentrated aqueous ammonia at 150 C to 7-methoxy-1,2,3,4-tetrahydroacridine-9-carboxamide (VII), followed by a Hoffman degradation with potassium hypobromite.

参考文献No.60339
标题:Tacrine
作者:Casta馿r, R.M.; Serradell, M.N.; Casta馿r, J.
来源:Drugs Fut 1987,12(11),1032
合成路线图解说明:

By cyclocondensation of 2-aminobenzonitrile (I) with cyclohexanone (II) by means of ZnCl2 at high temperature.

合成路线图解说明:

By nitration of acridine N-oxide (III) with H2SO4 - HNO3 to the corresponding 9-nitroacridine N-oxide (IV), followed by reduction with Fe - acetic acid.

合成路线图解说明:

By cyclocondensation of isatine (V) with cyclohexanone (II) and aqueous concentrated NH3 at 150 C in a pressure vessel to acridine-9-carboxamide (VI), followed by a Hoffman degradation with Br2 and sodium methoxide in methanol

合成路线图解说明:

The cyclocondensation of aniline (VII) with ethyl 2-oxocyclo-hexanecarboxylate (VIII) by means of HCl in refluxing benzene gives 9-acridone (IX), which by treatment with refluxing POCl3 is converted to 9-chloroacridine (X). Finally, this compound is treated with anhydrous NH3 in p-cresol), or with ethanolic ammonia with a Cu catalyst.

参考文献No.97189
标题:Analogues of 9-amino-1,2,3,4-tetrahydroacridine
作者:Bielavsky, J.
来源:Coll Czech Chem Commun 1977,422802-7
合成路线图解说明:

By cyclocondensation of isatine (V) with cyclohexanone (II) and aqueous concentrated NH3 at 150 C in a pressure vessel to acridine-9-carboxamide (VI), followed by a Hoffman degradation with Br2 and sodium methoxide in methanol

合成路线图解说明:

This compound can be prepared by two different methods: 1) By cyclocondensation of p-anisidine (I) with 2-oxocyclohexanecarboxylate (II) to 7-methoxy-1,2,3,4-tetrahydroacridone (III), which by treatment with refluxing POCl3 is converted to 9-chloro-7-methoxy-1,2,3,4-tetrahydroacridine (IV). This compound is converted to final product by treatment with NH3 in refluxing p-cresol. 2) By cyclocondensation of 5-methoxyisatin (V) and cyclohexanone (VI) in concentrated aqueous ammonia at 150 C to 7-methoxy-1,2,3,4-tetrahydroacridine-9-carboxamide (VII), followed by a Hoffman degradation with potassium hypobromite.

参考文献No.700480
标题:
作者:Morrison, L.; et al.
来源:Tetrahedron Lett 1963,20(4),1277-1281
合成路线图解说明:

By cyclocondensation of 2-aminobenzonitrile (I) with cyclohexanone (II) by means of ZnCl2 at high temperature.

参考文献No.700481
标题:Process for preparing substituted lactones of 2-(2'-hydroxyethyl)nicotinic acid or their N-oxides
作者:Klimov, G.A.; Makareva, T.N.; Tilichenko, M.N.; Shepetova, N.M.
来源:SU 463323
合成路线图解说明:

By nitration of acridine N-oxide (III) with H2SO4 - HNO3 to the corresponding 9-nitroacridine N-oxide (IV), followed by reduction with Fe - acetic acid.

参考文献No.700483
标题:
作者:Haslinger, B.; et al.
来源:J Chem Listy 1957,51(5),1906
合成路线图解说明:

By cyclocondensation of isatine (V) with cyclohexanone (II) and aqueous concentrated NH3 at 150 C in a pressure vessel to acridine-9-carboxamide (VI), followed by a Hoffman degradation with Br2 and sodium methoxide in methanol

参考文献No.700484
标题:
作者:Greenspan, S.; et al.
来源:J Collect Czech Chem Commun 1958,23(10),1319
合成路线图解说明:

By cyclocondensation of isatine (V) with cyclohexanone (II) and aqueous concentrated NH3 at 150 C in a pressure vessel to acridine-9-carboxamide (VI), followed by a Hoffman degradation with Br2 and sodium methoxide in methanol

参考文献No.700485
标题:
作者:Hottelart, C.; et al.
来源:J Chem Soc 1947,92(3),634-637
合成路线图解说明:

The cyclocondensation of aniline (VII) with ethyl 2-oxocyclo-hexanecarboxylate (VIII) by means of HCl in refluxing benzene gives 9-acridone (IX), which by treatment with refluxing POCl3 is converted to 9-chloroacridine (X). Finally, this compound is treated with anhydrous NH3 in p-cresol), or with ethanolic ammonia with a Cu catalyst.

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