1,2,3-Triazole-4-carbaldehydes are useful synthetic intermediates which may play an important role in the discovery of novel applications of the 1,2,3-triazole moiety. In this work, a one-step multigram scale synthesis of 4-formyl-1-(4-nitrophenyl)-1H-1,2,3-triazole (FNPT) as a preferred reagent for the synthesis of 1-alkyl-4-formyltriazoles is described, making use of the commercially available 3-dimethylaminoacrolein and 4-nitrophenyl azide. Next, the earlier reported reaction of FNPT with alkylamines is further explored, and for hexylamine, the one-pot sequential cycloaddition and Cornforth rearrangement is demonstrated. In addition, a useful protocol for the in situ diazotization of 4-nitroaniline is provided. This facilitated the complete hydrolysis of rearranged 4-iminomethyl-1,2,3-triazoles and allowed for the recycling of 4-nitrophenyl azide.

中文翻译：

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1-(4-Nitrophenyl)-1H-1,2,3-Triazole-4-carbaldehyde：可扩展合成及其在制备 1-Alkyl-4-Formyl-1,2,3-triazoles 中的应用

1,2,3-三唑-4-甲醛是有用的合成中间体，在发现1,2,3-三唑部分的新应用方面可能发挥重要作用。在这项工作中，4-甲酰基-1-(4-硝基苯基)-1 H的一步多克规模合成-1,2,3-三唑 (FNPT) 作为合成 1-烷基-4-甲酰基三唑的优选试剂被描述，利用可商购的3-二甲氨基丙烯醛和4-硝基苯基叠氮化物。接下来，进一步探索了早先报道的 FNPT 与烷基胺的反应，对于己胺，证明了一锅顺序环加成和 Cornforth 重排。此外，还提供了 4-硝基苯胺原位重氮化的有用协议。这促进了重排的 4-亚氨基甲基-1,2,3-三唑的完全水解，并允许循环使用 4-硝基苯基叠氮化物。