Generation and application of carbodiimide anions: efficient construction of 2-aminopyrimidines via a cascade [4 + 2] annulation/aromatization sequence†
Chuan-Chuan Wang, Xin-Lu Wang, Qing-Long Wang, Yi-Zhi Gong, Xue-Hui Hou, Jun-Tao Liu and Ya-Jing Chen
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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.
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.
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