Divergent [5 + 1] Annulation of o-Aminobenzamides with Vinylene Carbonate as a Multifunctional Reagent

IF 3.6 2区 化学 Q1 CHEMISTRY, ORGANIC Journal of Organic Chemistry Pub Date : 2025-04-03 DOI:10.1021/acs.joc.5c00039
Jiang Nan, Hanqing Zhang, Lanxin Zhu, Shilei Liu, Qiang Yan
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Abstract

A divergent [5 + 1] cyclization reaction of o-aminobenzamides with vinylene carbonate has been developed, rapidly generating three types of cyclic molecules including quinazolinones, 2-methylquinazolinones, and 2,3-dihydroquinazolinones with high chemoselectivity. In this discovery, vinylene carbonate blooms as a multifunctional reagent to participate in cyclization. The potential of this new finding is further emphasized by assembling the benzothiazole heteroarene via the [4 + 1] version and tolerating bioactive units well.

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邻氨基苯甲酰胺与作为多功能试剂的碳酸亚乙烯酯的歧化 [5 + 1] 嵌合反应
邻氨基苯并胺类化合物与碳酸乙烯酯发生了[5 + 1]分散环化反应,快速生成了具有高化学选择性的三种环分子:喹唑啉酮类、2-甲基喹唑啉酮类和2,3-二氢喹唑啉酮类。在这一发现中,碳酸乙烯作为一种多功能试剂参与环化。这一新发现的潜力进一步强调了通过[4 + 1]版本组装苯并噻唑杂芳烃和耐受良好的生物活性单位。
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来源期刊
Journal of Organic Chemistry
Journal of Organic Chemistry 化学-有机化学
CiteScore
6.20
自引率
11.10%
发文量
1467
审稿时长
2 months
期刊介绍: Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.
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