Regio-and Stereoselective Azidation of Activated N-allenamides: an entry to , ,  and -amido-azides.

IF 4.6 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2024-11-04 DOI:10.1039/d4qo01802h

Dorian Schutz, Maxime Hourtoule, Laurence Miesch

引用次数: 0

Abstract

A totally controlled regiodivergent azidation of activated N-allenamides is presented. Using TMSN3/TBAF, β-azidation of N-allenamides occurs exclusively, yielding vinyl azides. Conversely, employing a TFA/TMSN3 mixture results solely in the formation of γ-azides. A subsequent formal Winstein rearrangement of the latter with DBU produces α-amido vinyl azides. Additionally, δ-difluorinated azides featuring an ynamide are selectively synthesized from ene-ynamides. The practical applicability of these transformations is demonstrated through the formation of cyanide derivatives, trifluoromethyl ketones and primary enamines.

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活化 N-烯酰胺的区域和立体选择性叠氮：进入 、、 和 -氨基氮。

本文介绍了活化 N-allenamides 的一种完全受控的区域发散唑化反应。使用 TMSN3/TBAF 时，N-烯酰胺只发生 β-叠氮反应，生成乙烯基叠氮化物。相反，使用 TFA/TMSN3 混合物则只生成γ-叠氮化物。后者随后与 DBU 发生形式温斯坦重排，生成 α-氨基乙烯基叠氮化物。此外，还可以从烯酰胺中选择性地合成具有酰酰胺特征的 δ-二氟叠氮化物。通过形成氰化物衍生物、三氟甲基酮和伯胺，证明了这些转化的实际应用性。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

期刊介绍： Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.