- Steric Effect Determines the Formation of Lactam-Lactam Dimers or Amide C.O···NH (Lactam) Chain Motifs in N-Phenyl-2-hydroxynicotinanilides
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A series of N-phenyl-2-hydroxynicotinanilides (PHNAs) have been synthesized, and their crystal structures have been investigated. The identity of these compounds is revealed to be the tautomer of PHNAs, i.e., 2-oxo-1,2-dihydropyridine-3-carboxylic acid phenylamides, compounds with both amide and lactam functionalities. Among these compounds, those with no or negligible steric hindrance take a near planar conformation and form lactam-lactam dimers, not the widely observed amide NH···O=C hydrogen bond chains, while those with steric hindrance take a twisted conformation and form an amide NH···O=C (lactam) hydrogen bond. A succinct theoretic study combining conformational analysis and molecular electrostatic potential surfaces (MEPS) survey provided a reasonable explanation of the formation of these two different hydrogen bond motifs.
- Cao, S.,Chen, J.,Li, T.,Liu, H.,Long, S.,Parkin, S.,Yang, X.,Yang, Z.,Yu, F.,Zhang, M.
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- One-pot synthesis of n-aryl-nicotinamides and diarylamines based on a tunable smiles rearrangement
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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. 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.
- Liu, Shihui,Zhu, Shaofan,Wu, Ying,Gao, Jiayu,Qian, Pengfei,Hu, Yanwei,Shi, Linsen,Chen, Shaohua,Zhang, Shilei,Zhang, Yinan
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supporting information
p. 3048 - 3052
(2015/05/13)
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