Generation and application of carbodiimide anions: efficient construction of 2-aminopyrimidines via a cascade [4 + 2] annulation/aromatization sequence†

IF 4.6 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2023-10-11 DOI:10.1039/D3QO01604H

Chuan-Chuan Wang, Xin-Lu Wang, Qing-Long Wang, Yi-Zhi Gong, Xue-Hui Hou, Jun-Tao Liu and Ya-Jing Chen

引用次数: 0

Abstract

The cascade [4 + 2] annulation/aromatization reactions between carbodiimide anions and α,β-unsaturated imines are developed. This is the first report on regulating N-Ts cyanamides to participate in reactions absolutely via carbodiimide anions rather than previously reported cyanamide anions, affording a convenient method for synthesizing 2-aminopyrimidines. More importantly, this work expands the application of carbodiimides, broadening the coupling substrate scope to electrophilic partners and providing new strategies to construct six-membered N-heteroaromatic scaffolds. A stepwise mechanism, supported by DFT calculations, is invoked to explain the reaction selectivity.

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碳二亚胺阴离子的生成和应用:通过级联[4+2]环/芳构化序列高效构建2-氨基嘧啶

本工作揭示了一种前所未有的碳二亚胺阴离子参与级联[4 + 2]环化/芳构化反应，为合成2-氨基嘧啶提供了一种有效的方法。

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.