Copper-catalyzed one-pot coupling reactions of aldehydes (ketones), tosylhydrazide and 2-amino(benzo)thiazoles: An efficient strategy for the synthesis of N-alkylated (benzo)thiazoles
Copper-catalyzed one-pot coupling reactions of aldehydes (ketones), tosylhydrazide and 2-amino(benzo)thiazoles: An efficient strategy for the synthesis of N-alkylated (benzo)thiazoles
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铜催化醛（酮）、甲苯磺酰肼和2-氨基（苯并）噻唑的一锅偶联反应：合成N-烷基化（苯并）噻唑的有效策略
DOI：
10.1002/aoc.5124
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发表时间：
2019
影响因子：
3.9
通讯作者：
Wang Cunde
中科院分区：
文献类型：
--
作者：
Xie Zengyang;Chen Ruijiao;Ma Mingfang;Kong Lingdong;Liu Jun;Wang Cunde
以2-氨基（苯并）噻唑和醛（酮）为原料，通过铜催化的一锅两步反应合成了N-烷基化（苯并）噻唑类化合物。这种交叉偶联反应顺利进行，并耐受广泛的官能团（46个实例）。以中到高产率得到了多种官能化的N-烷基化（苯并）噻唑。值得注意的是，通过该方案还实现了法尼唑（抗炎药）的克级合成。
An efficient and practical C–N bond formation methodology for the synthesis ofN‐alkylated (benzo)thiazoles was developed, via the copper‐catalyzed one‐pot two‐step reactions of 2‐amino(benzo)thiazoles and aldehydes (ketones) with tosylhydrazide. This cross‐coupling reaction proceeded smoothly and tolerated a broad range of functional groups (46 examples). A variety of functionalizedN‐alkylated (benzo)thiazoles were obtained in moderate to high yields. Notably, gram‐scale synthesis of fanetizole (anti‐inflammatory drug) was also realized through this protocol.