由2-氮二烯-氧二烯（4 + 1）环加成的2h -氮嘧啶、重氮化合物和m-CPBA一锅模块化合成3-恶唑啉

IF 4.7 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2025-06-24 DOI:10.1039/d5qo00717h

Ilya P. Filippov, Mikhail Sergeevich Novikov, Nikolai V. Rostovskii

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引用次数: 0

摘要

2-阿扎布塔-1,3-二烯与间氯过氧苯甲酸在温和条件下反应生成3-恶唑啉时，氧烯发生了正式的（4 + 1）环加成。从机理上讲，该反应是一个扩展的Prilezhaev反应，包括形成先前未知的（1-氮杂乙烯基）氧环，然后是酸催化的环扩张。从Cu(II)-或Rh(II)-催化的2h -氮嘧啶与重氮化合物的反应开始，该环加成用于一锅法合成密集取代的3-恶唑啉，这是其他方法无法达到的。

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One-pot modular synthesis of 3-oxazolines from 2H-azirines, diazo compounds, and m-CPBA enabled by 2-azadiene–oxene (4 + 1) cycloaddition

A formal (4 + 1) cycloaddition of oxene occurs in the reaction of 2-azabuta-1,3-dienes with m-chloroperoxybenzoic acid under mild conditions to give 3-oxazolines. Mechanistically, the reaction is an extended Prilezhaev reaction involving the formation of previously unknown (1-azavinyl)oxiranes, followed by the acid-catalyzed ring expansion. This cycloaddition was used for the one-pot synthesis of densely substituted 3-oxazolines, inaccessible by other protocols, starting from Cu(II)- or Rh(II)-catalyzed reaction of 2H-azirines with diazo compounds.

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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.