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| N-Methylindole was found to react smoothly with iodo-benzene providing an excellent yield (96%) of the C-2 ary-lated product. The reaction also worked well with an electron withdrawing substituent such as nitro on the aryl iodide (entry 2). To check the generality of the procedure the system was extended to various azoles including benzo-thiazole, thiazole, benzoxazole, oxazole and triazole (entries 3–11). Benzothiazole was found to react e ciently with both iodo and the less reactive bromoarene providing good yields of the desired product. Also, electron donating groups such as methyl and methoxy at the ortho or para positions of the iodoarene were viable partners under the present conditions (entries 5, 7, and 10). 1-Methyltriazole was found to be arylated selectively at the more active C-5 position (entry 11). We also tested the applicability of this method with other heteroarenes such as benzothio-phene and benzofuran (entries 12–15). However, reaction of benzothiophene was found to be sluggish using the pre-sent catalytic system, while benzofuran was found to react e ciently with both iodo and bromobenzene providing good yields of the desired product. Encouraged with the above results, the system was further extended to the aryaltion of ca eine, as the products are of interest as adenosine receptor antagonists. Ca eine was arylated e ectively under the present conditions providing an excel-lent yield of 60% of product (entry 16). If C–H activation methodology is not used, the synthetic sequence leading to these compounds requires several steps instead of a single step. |
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cfk580713
至尊木虫 (著名写手)
- 翻译EPI: 277
- 应助: 30 (小学生)
- 贵宾: 0.038
- 金币: 13604.3
- 散金: 123
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- 帖子: 1258
- 在线: 826.9小时
- 虫号: 253096
- 注册: 2006-05-20
- 性别: GG
- 专业: 有机高分子功能材料
【答案】应助回帖
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张超峰: 金币+45, 翻译EPI+1 2012-05-08 09:23:52
张超峰: 金币+45, 翻译EPI+1 2012-05-08 09:23:52
| 研究发现，N-甲基吲哚可以与碘代苯发生C-2芳基化反应，产率高达96%。该反应在带有强拉电子取代基的芳基吲哚体系中(entry 2). 为了检验该过程的普适性，同时考察了各种唑类化合物，包括苯并噻唑，噻唑，苯并恶唑，噁唑以及三唑(entries 3–11). 实验结果表明，苯并噻唑与吲哚以及活性更低的溴代芳烃间都能发生有效的化学反应并以高产率得到目标产物。 |
2楼2012-05-07 22:28:57
cfk580713
至尊木虫 (著名写手)
- 翻译EPI: 277
- 应助: 30 (小学生)
- 贵宾: 0.038
- 金币: 13604.3
- 散金: 123
- 红花: 6
- 帖子: 1258
- 在线: 826.9小时
- 虫号: 253096
- 注册: 2006-05-20
- 性别: GG
- 专业: 有机高分子功能材料
【答案】应助回帖
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张超峰: 金币+40 2012-05-08 09:24:00
张超峰: 金币+40 2012-05-08 09:24:00
| 同时，也研究了邻、对位给电子取代基如甲基，甲氧基的影响(entries 5, 7, and 10). 结果表明，1-甲基三唑选择性的在高活性的C-5位上发生芳基化1(entry 11). 我们也检验了该方法在其他杂环芳烃如苯并噻吩，苯并呋喃体系中的适用性(entries 12–15). 虽然在现有催化体系中，发现苯并噻吩的反应是很慢的，而苯并呋喃与吲哚以及活性更低的溴代芳烃间都能发生有效的化学反应并以高产率得到目标产物。基于以上实验结果，该体系又扩展到了ca eine的芳化，因为它们的反应产物可作为有用的腺苷受体拮抗剂。 |
3楼2012-05-07 22:40:16
cfk580713
至尊木虫 (著名写手)
- 翻译EPI: 277
- 应助: 30 (小学生)
- 贵宾: 0.038
- 金币: 13604.3
- 散金: 123
- 红花: 6
- 帖子: 1258
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- 虫号: 253096
- 注册: 2006-05-20
- 性别: GG
- 专业: 有机高分子功能材料
4楼2012-05-07 22:44:38
