A Four‐Component Reaction Strategy for Pyrimidine Carboxamide Synthesis. Issue 5 (14th December 2016)

• Record Type: Journal Article
• Authors: Guo, Wei; Liao, Jianhua; Liu, Dongqing; Li, Jiawei; Ji, Fanghua; Wu, Wanqing; Jiang, Huanfeng
• Is Part Of: Angewandte Chemie international edition. Volume 56:Issue 5(2017)
• Page Start: 1289
• Page End: 1293
• Publication Date: 2016-12-14
• Subjects: cyclization -- heterocycles -- multicomponent reactions -- palladium -- synthons; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201608433
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: 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. Abstract : Three to four to one : A palladium‐catalyzed oxidative 3 starting materials–4 component reaction (3SM‐4CR) strategy for the synthesis of pyrimidine carboxamides from amidines, styrene, and DMF. DMF serves as a dual synthon, a one‐carbon‐atom synthon and amide synthon. This is a fascinating protocol for the preparation of pyrimidine carboxamides and has potential applications in the pharmaceutical industry.