Facile synthesis of benzo[e][1,2,4]triazepin-5-ones through a base medicated [4+3] cycloaddition

IF 2.2 3区 化学 Q2 CHEMISTRY, ORGANIC Tetrahedron Pub Date : 2025-07-01 Epub Date: 2025-04-03 DOI:10.1016/j.tet.2025.134595
Eeda lingareddy , Ravindra M. Kumbhare
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Abstract

Herein, we report the synthesis of highly functionalized benzo[e][1,2,4]triazepin-5-ones through a base medicated [4 + 3] cycloaddition of hydrazonoyl chloride and isatoic anhydride. The reaction proceeds through in situ generated nitrile imines from easily accessible hydrazonoyl chlorides. a simple organic base triethyl amine drives the reaction very successfully to give the desired products in excellent yields. The robustness of the [4 + 3] cycloaddition process is well evidented by broad substrate scope.

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碱[4+3]环加成法合成苯并[e][1,2,4]三氮平-5- 1
在此,我们报告了通过肼酰氯和异酸酐的碱[4 + 3]环加成法合成高官能化苯并[e][1,2,4]三氮杂卓-5-酮的过程。该反应是通过容易获得的肼酰氯原位生成腈亚胺进行的。一种简单的有机碱三乙基胺成功地推动了反应的进行,以极好的收率得到了所需的产物。广泛的底物范围充分证明了 [4 + 3] 环加成过程的稳健性。
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来源期刊
Tetrahedron
Tetrahedron 化学-有机化学
CiteScore
3.90
自引率
4.80%
发文量
439
审稿时长
34 days
期刊介绍: Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry. Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters. Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.
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