81685-47-4Relevant academic research and scientific papers
Steric Effect Determines the Formation of Lactam-Lactam Dimers or Amide C.O···NH (Lactam) Chain Motifs in N-Phenyl-2-hydroxynicotinanilides
Cao, S.,Chen, J.,Li, T.,Liu, H.,Long, S.,Parkin, S.,Yang, X.,Yang, Z.,Yu, F.,Zhang, M.
, p. 4346 - 4357 (2020/07/14)
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.
One-pot synthesis of n-aryl-nicotinamides and diarylamines based on a tunable smiles rearrangement
Liu, Shihui,Zhu, Shaofan,Wu, Ying,Gao, Jiayu,Qian, Pengfei,Hu, Yanwei,Shi, Linsen,Chen, Shaohua,Zhang, Shilei,Zhang, Yinan
supporting information, p. 3048 - 3052 (2015/05/13)
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.
KOtBu mediated synthesis of phenanthridinones and dibenzoazepinones
Bhakuni, Bhagat Singh,Kumar, Amit,Balkrishna, Shah Jaimin,Sheikh, Javeed Ahmed,Konar, Sanjit,Kumar, Sangit
supporting information; experimental part, p. 2838 - 2841 (2012/07/28)
Synthesis of substituted phenanthridinones and dibenzoazepinones has been realized from 2-halo-benzamides in the presence of potassium tert-butoxide and a catalytic amount of 1,10-phenanthroline or AIBN. This new carbon-carbon bond forming reaction gives direct access to various biaryl lactams containing six- and seven-membered rings chemoselectively. Carbon-carbon coupling seems to proceed by the generation of a radical in the amide ring which leads to C-H arylation of aniline.
ORGANIC COMPOUNDS
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Page/Page column 19, (2009/07/03)
The present invention provides heterocyclic derivatives that modulate the activity of stearoyl-CoA desaturase. Methods of using such derivatives to modulate the activity of stearoyl-CoA desaturase and pharmaceutical compositions comprising such derivatives are also encompassed.
A Convenient Synthesis of N-Aryl-1,2-dihydro-2-oxo-3-pyridinecarboxamides, N-Aryl-N-methyl-1,2-dihydro-2-oxo-3-pyrimidinecarboxamides and Their 1-Methyl (O-Methyl)-Derivatives
Cativiela, C,Fernandez, J.,Melendez, E.
, p. 1093 - 1097 (2007/10/02)
A new and versatile method for the preparation of the isonixine analogous, N-aryl-1,2-dihydro-2-oxo-3-pyridinecarboxamides and N-aryl-N-methyl-1,2-dihydro-2-oxo-3-pyridinecarboxamides is described via the selective chlorination of 2-hydroxynicotinic acid.
