Amines, especially those with multi-nitrogen moieties, are widespread in natural products and biologically active compounds. Thus, the development of direct and efficient methods to introduce multiple nitrogen-containing fragments into compounds in one step is highly desirable yet challenging. Herein, we report an NIS-promoted selective amino-diazidation and amino-iodoazidation of O-homoallyl benzimidates with NaN₃. By using this protocol, a variety of vicinal diazido-substituted 1,3-oxazines and vicinal iodoazido-substituted 1,3-oxazines were directly synthesized in a controllable manner. Preliminary mechanistic investigations revealed that the reaction operates through a NIS-promoted four-step cascade process. The developed method has the merits of metal-free, excellent functional group compatibility, simple operation, and mild conditions.

中文翻译：

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NIS 促进的 O-Homoallyl Benzimidates 的选择性氨基二叠氮化和氨基碘叠氮化：邻位二叠氮基 1,3-恶嗪和邻位碘叠氮基 1,3-恶嗪的合成

胺类，尤其是具有多氮部分的胺类，广泛存在于天然产物和生物活性化合物中。因此，非常需要开发一种直接有效的方法，将多个含氮片段一步引入化合物中，但也具有挑战性。在此，我们报告了 NIS 促进的O -homoallyl benzimidates 与 NaN ₃的选择性氨基二叠氮化和氨基碘叠氮化. 通过使用该协议，以可控方式直接合成了多种邻位二叠氮基取代的 1,3-恶嗪和邻位碘叠氮基取代的 1,3-恶嗪。初步的机理研究表明，该反应通过 NIS 促进的四步级联过程进行。该方法具有无金属、官能团相容性好、操作简单、条件温和等优点。