A Four‐Component Reaction Strategy for Pyrimidine Carboxamide Synthesis,Angewandte Chemie International Edition

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A Four‐Component Reaction Strategy for Pyrimidine Carboxamide Synthesis
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2016-12-14 , DOI: 10.1002/anie.201608433
Wei Guo _{1,

2} , Jianhua Liao ₁ , Dongqing Liu ₁ , Jiawei Li ₁ , Fanghua Ji ₁ , Wanqing Wu ₁ , Huanfeng Jiang ₁

Affiliation

Demonstrated herein is a highly effective 3 starting materials–4 component reaction (3SM‐4CR) strategy for the synthesis of pyrimidine carboxamides from amidines, styrene, and N,N‐dimethylformamide (DMF) by a palladium‐catalyzed oxidative process. This transformation represents the first example of employing DMF as a dual synthon, a one‐carbon‐atom synthon and amide synthon, and was proven by isotope‐labeling experiments. Additionally, the combination of C−H bond functionalization and cross‐dehydrogenative coupling processes affords four chemical bond formations. This sequential 3SM‐4CR strategy features inexpensive, readily available starting materials, green oxidants, as well as atom and step economy. It leads to the preparation of pyrimidine carboxamides and has potential applications in the pharmaceutical industry.

中文翻译：

嘧啶甲酰胺合成的四组分反应策略

本文展示了一种由3，苯乙烯和N，N合成嘧啶羧酰胺的高效3原料-4组分反应（3SM-4CR）策略钯催化的氧化过程生成二甲基甲酰胺（DMF）。这种转化代表了将DMF用作双重合成子，一个碳原子合成子和酰胺合成子的第一个例子，并通过同位素标记实验得到了证明。此外，CH键功能化和交叉脱氢偶联过程的结合提供了四个化学键的形成。这种顺序的3SM-4CR策略具有廉价，易于获得的起始原料，绿色氧化剂以及原子和步骤经济的特点。它导致了嘧啶羧酰胺的制备，并在制药工业中具有潜在的应用。

更新日期：2016-12-14

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