【结 构 式】 |
【分子编号】33786 【品名】2-[4-chloro-2-[(Z)hydrazono(4-nitrophenyl)methyl]phenyl]acetic acid 【CA登记号】 |
【 分 子 式 】C15H12ClN3O4 【 分 子 量 】333.7308 【元素组成】C 53.99% H 3.62% Cl 10.62% N 12.59% O 19.18% |
合成路线1
该中间体在本合成路线中的序号:(V)Condensation of 2-(4-chlorophenyl)ethanol (I) with 4-nitrobenzaldehyde (II) by means of ZnCl2 and HCl produced isochromane (III). Subsequent oxidative cleavage of (III) employing Jones reagent in acetone afforded ketoacid (IV). Conversion of (IV) to the corresponding hydrazone (V), followed by cyclization in the presence of dicyclohexylcarbodiimide yielded benzodiazepinone (VI). After conversion of (VI) to the benzodiazepine thione (VII) by treatment with P2S5, condensation with 2-(1-aminoethyl)-1,3-dioxolane (VIII) employing HgO as the desulfurizing reagent furnished (IX). Further acid-catalyzed cyclization of (IX) gave rise to the imidazobenzodiazepine (X). Finally, the nitro group of (X) was reduced by transfer hydrogenation using hydrazine and Raney Nickel.
【1】 Csuazdi, E.; Solyom, S.; Abraham, G.; et al.; New non competitive AMPA antagonists. Bioorg Med Chem 2000, 8, 8, 2127. |
【2】 Csuzdi, E.; Ling, I.; Berzsenyi, P.; Horvath, K.; Abraham, G.; Andrasi, F.; Hamori, T.; Moravcsik, I.; Simay, A.; Tarnawa, I.; Pallagi, I.; Solyom, S. (Gyogyszerkutato Intezet Kft.); New 2,3-benzodiazepine derivs.. EP 1001956; WO 9906408 . |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(I) | 33783 | 2-(4-chlorophenyl)-1-ethanol | 1875-88-3 | C8H9ClO | 详情 | 详情 |
(II) | 18184 | 4-Nitrobenzaldehyde | 555-16-8 | C7H5NO3 | 详情 | 详情 |
(III) | 33784 | 7-chloro-1-(4-nitrophenyl)-3,4-dihydro-1H-isochromene | C15H12ClNO3 | 详情 | 详情 | |
(IV) | 33785 | 2-[4-chloro-2-(4-nitrobenzoyl)phenyl]acetic acid | C15H10ClNO5 | 详情 | 详情 | |
(V) | 33786 | 2-[4-chloro-2-[(Z)hydrazono(4-nitrophenyl)methyl]phenyl]acetic acid | C15H12ClN3O4 | 详情 | 详情 | |
(VI) | 33787 | 8-chloro-1-(4-nitrophenyl)-3,5-dihydro-4H-2,3-benzodiazepin-4-one | C15H10ClN3O3 | 详情 | 详情 | |
(VII) | 33788 | 8-chloro-1-(4-nitrophenyl)-3,5-dihydro-4H-2,3-benzodiazepine-4-thione | C15H10ClN3O2S | 详情 | 详情 | |
(VIII) | 33789 | 1-(1,3-dioxolan-2-yl)-1-ethanamine; 1-(1,3-dioxolan-2-yl)ethylamine | C5H11NO2 | 详情 | 详情 | |
(IX) | 33790 | 8-chloro-N-[1-(1,3-dioxolan-2-yl)ethyl]-1-(4-nitrophenyl)-5H-2,3-benzodiazepin-4-amine; N-[8-chloro-1-(4-nitrophenyl)-5H-2,3-benzodiazepin-4-yl]-N-[1-(1,3-dioxolan-2-yl)ethyl]amine | C20H19ClN4O4 | 详情 | 详情 | |
(X) | 33791 | 8-chloro-2-methyl-6-(4-nitrophenyl)-11H-imidazo[1,2-c][2,3]benzodiazepine | C18H13ClN4O2 | 详情 | 详情 |