Synthesis of nitrogen-containing Spirocycles via Superacid-promoted Cyclizations of imines

IF 1.5 4区 化学 Q3 CHEMISTRY, ORGANIC Tetrahedron Letters Pub Date : 2025-05-15 Epub Date: 2025-03-27 DOI:10.1016/j.tetlet.2025.155551
Mariam Mutiu Adebayo, Douglas A. Klumpp
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Abstract

Aromatic imines were prepared from 9-fluorenone and azafluorenones and these substrates were reacted in the Brønsted superacid, triflic acid, to produce good yields of nitrogen-containing spirocycles. A mechanism is proposed involving dicationic, superelectrophilic intermediates. The resulting spirocycles may be easily functionalized at nitrogen to prepared amides, sulfonamides, and other derivatives.

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超强酸促进亚胺环化合成含氮螺环
以9-芴酮和氮杂芴酮为原料制备芳香亚胺,并在Brønsted超羧酸三叶酸中反应,得到含氮螺环化合物的高产率。提出了一种涉及指示性超亲电中间体的机理。所得到的螺环可以很容易地在氮上官能化成制备的酰胺、磺胺和其他衍生物。
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来源期刊
Tetrahedron Letters
Tetrahedron Letters 化学-有机化学
CiteScore
3.50
自引率
5.60%
发文量
521
审稿时长
28 days
期刊介绍: Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.
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