Herein, we report a conceptually new, general, and efficient approach for the synthesis of valuable ortho‐azido‐1,5‐disubstituted tetrazole and one‐pot synthesis of ortho‐triazoletetrazole derivatives mainly via PIDA mediated N‐N cleavage of the azole ring of 2H‐indazoles using TMSN3. This current methodology represents an array of unsymmetrical ortho‐azidotetrazole and ortho‐triazoletetrazole derivatives with wide functional group tolerance in good to excellent yields under mild reaction conditions. The practical utility of this reaction was showcased through successful scale‐up synthesis and a variety of subsequent derivatizations of ortho‐azidotetrazole products. Mechanistic investigations indicate that the reaction proceeds through a radical pathway.

中文翻译：

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唑类化合物的多样化合成：通过 2H-吲哚唑的 N-N 裂解构建邻位叠氮基四唑/三唑四唑


在此，我们报告了一种概念上新颖、通用且有效的方法，用于合成有价值的邻叠氮基-1,5-二取代四唑和邻三唑四唑衍生物的一锅法合成，主要通过 PIDA 介导的 N-N 裂解使用 TMSN3 对 2H-吲哚唑的唑环进行切割。目前的这种方法代表了一系列不对称的邻叠氮四唑和邻三唑四唑衍生物，在温和的反应条件下具有广泛的官能团耐受性，产率从好到极好。该反应的实际用途通过成功的放大合成和邻叠氮基四唑产物的各种后续衍生化展示了。机理研究表明，反应通过自由基途径进行。