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【结 构 式】 
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【分子编号】64301 【品名】methyl 4-chloro-5-({[3-(dimethylamino)propyl]anilino}carbonyl)thieno[2,3-b]thiophene-2-carboxylate 【CA登记号】 |
【 分 子 式 】C20H21ClN2O3S2 【 分 子 量 】436.98312 【元素组成】C 54.97% H 4.84% Cl 8.11% N 6.41% O 10.98% S 14.68% |
合成路线1
该中间体在本合成路线中的序号：(VIII)Jones oxidation of 4-bromothiophene-2-carbaldehyde (I) leads to acid (II), which is further esterified with H2SO4/MeOH to furnish methyl 4-bromothiophene-2-carboxylate (III). Subsequent Heck coupling of aryl bromide (III) with cyclohexylammonium acrylate (IV) gives rise to the thienylacrylic acid (V). Cyclization of (V) with SOCl2 in the presence of pyridine produces the thienothiophene derivative (VI). Acid chloride (VI) is then coupled to N-(dimethylaminopropyl)aniline (VII) under Schotten-Baumann conditions, yielding amide (VIII). Finally, photochemical cyclization of (VIII) affords the target tetracyclic compound.
| 【1】 DoganKoruznjak, J.; Slade, N.; Zamola, B.; Pavelic, K.; Karminski-Zamola, G.; Synthesis, photochemical synthesis and antitumor evaluation of novel derivatives of thieno[3',2':4,5]thieno[2,3-c]quinolones. Chem Pharm Bull 2002, 50, 5, 656. |
| 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) | 24142 | 4-bromo-2-thiophenecarbaldehyde | 18791-75-8 | C5H3BrOS | 详情 | 详情 |
| (II) | 64296 | 4-bromo-2-thiophenecarboxylic acid | C5H3BrO2S | 详情 | 详情 | |
| (III) | 64297 | methyl 4-bromo-2-thiophenecarboxylate | C6H5BrO2S | 详情 | 详情 | |
| (IV) | 19139 | acrylic acid | 79-10-7 | C3H4O2 | 详情 | 详情 |
| (V) | 64298 | (E)-3-[5-(methoxycarbonyl)-3-thienyl]-2-propenoic acid | C9H8O4S | 详情 | 详情 | |
| (VI) | 64299 | methyl 4-chloro-5-(chlorocarbonyl)thieno[2,3-b]thiophene-2-carboxylate | C9H4Cl2O3S2 | 详情 | 详情 | |
| (VII) | 64300 | N-(3-anilinopropyl)-N,N-dimethylamine; N~1~,N~1~-dimethyl-N~3~-phenyl-1,3-propanediamine | C11H18N2 | 详情 | 详情 | |
| (VIII) | 64301 | methyl 4-chloro-5-({[3-(dimethylamino)propyl]anilino}carbonyl)thieno[2,3-b]thiophene-2-carboxylate | C20H21ClN2O3S2 | 详情 | 详情 |