One‐Pot Synthesis of N‐Aryl‐Nicotinamides and Diarylamines Based on a Tunable Smiles Rearrangement. Issue 14 (7th April 2015)

• Record Type: Journal Article
• Authors: Liu, Shihui; Zhu, Shaofan; Wu, Ying; Gao, Jiayu; Qian, Pengfei; Hu, Yanwei; Shi, Linsen; Chen, Shaohua; Zhang, Shilei; Zhang, Yinan
• Is Part Of: European journal of organic chemistry. Issue 14(2015)
• Page Start: 3048
• Page End: 3052
• Publication Date: 2015-04-07
• Subjects: Rearrangement -- Amines -- Amides­ -- Synthetic methods -- Heterocycles; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201500222
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A one‐pot Smiles rearrangement has been developed as a useful protocol for the straightforward synthesis of diverse N ‐aryl‐nicotinamides. This method also provides chemoselective access toward diarylamines based on the different substitutions of the amide group. The potential application of the transformation is exemplified by the synthesis of an on‐market succinate dehydrogenase inhibitor, boscalid. Abstract : A substituent‐mediated Smiles rearrangement to N ‐aryl‐nicotinamides and diarylamines has been developed. In addition to the wide range of heterocyclic building blocks, the one‐pot process also provides an efficient access to an on‐market fungicide, boscalid.