16582-88-0Relevant articles and documents
Synthesis and conformational analysis of N-aryl-N-(3-thienyl)acetamides
Ito, Ai,Asami, Yuki,Asato, Marino,Fukuda, Kazuo,Yamasaki, Ryu,Okamoto, Iwao
supporting information, p. 2454 - 2458 (2018/05/25)
The cis-trans conformational equilibrium of amides is of interest because it can be used to control functional activity. Here, we designed and synthesized a series of N-(3-thienyl)amides in order to study the factors affecting their conformational equilibrium. NMR studies showed that the major conformer of N-methyl-N-(3-thienyl)amide in solution is the E-form (cis form), as is the case for N-methylacetamide. For N-aryl-N-(3-thienyl)amides bearing an N-phenyl moiety, the major conformers differ depending on not only the relative π-electron density of the N-aryl moiety, but also its size. X-ray analysis showed that their solid-state conformational preferences were similar to those in solution.
Interaction of polyfluorinated 2-chloroquinolines with ammonia
Skolyapova, Alexandrina D.,Selivanova, Galina A.,Tretyakov, Evgeny V.,Bogdanova, Tatjana F.,Shchegoleva, Lyudmila N.,Bagryanskaya, Irina Yu.,Gurskaya, Larisa Yu.,Shteingarts, Vitalij D.
, p. 1219 - 1229 (2017/02/18)
We have studied the interaction of polyfluorinated (in the benzene moiety) 2-chloroquinolines with liquid and aqueous ammonia as an approach to the synthesis of halogen-containing aminoquinolines. 5,7-Difluoro-, 5,6,8-trifluoro-, and 5,7,8-trifluoro-2-chloroquinolines mostly form products of substitution of the Cl atom, whereas 5,7-difluoro-2,6-dichloroquinoline, 5,6,7,8-tetrafluoro-, and 6,7-difluoro-2-chloroquinolines yield products of substitution of an F atom at various positions. The replacement of liquid ammonia with aqueous causes an increase in the proportion of the products of aminodechlorination relative to the products of aminodefluorination. For 2-chloro-6,8-difluoroquinoline this replacement leads to 2-amino-6,8-difluoroquinoline as the main product instead of the 8-amino-derivative. Activation energy values estimated by DFT calculations for the reactions in question agree with the reaction regioselectivity observed experimentally.
Hydrodefluorination of N-acetylheptafluoro-2-naphthylamine by zinc in aqueous ammonia: Synthetic outcomes and mechanistic considerations
Reshetov, Alexey V.,Selivanova, Galina A.,Politanskaya, Larisa V.,Beregovaya, Irina V.,Shchegoleva, Lyudmila N.,Vasil'eva, Nadezhda V.,Bagryanskaya, Irina Yu.,Shteingarts, Vitalij D.
experimental part, p. 242 - 262 (2011/10/09)
Reduction of the N-acetyl derivatives of heptafluoro-2-naphthylamine and its less fluorinated analogues by zinc in aqueous NH3 has been investigated as a possible general and concise route to partially fluorinated N-(2-naphthyl)acetamides and, accordingly, 2-naphthylamines inaccessible by other ways. Quantum chemical calculations and CV measurement results have been used to discuss and justify the suggested reaction mechanism including two competing routes: fragmentation of a substrate radical anion and its complex with a zinc cation. ARKAT-USA, Inc.
