18542-98-8Relevant articles and documents
Substituent effects on the isomerization of hydrazone switches driven by the intramolecular hydrogen bond
Lu, Chaocao,Htan, Bu,Fu, Shitao,Ma, Chunmiao,Gan, Quan
, p. 4010 - 4016 (2019)
In this work, the substituent effects on hydrogen bonding in one kind of hydrazone-based switch are revealed. The E/Z isomerization ratios of these hydrazones and their intramolecular hydrogen bond strengths in the Z form were evaluated using NMR technique. Linear correlations between these parameters and Hammett empirical values for substituent effects are explored as well.
N-Heterocyclic Carbene Catalyzed Concerted Nucleophilic Aromatic Substitution of Aryl Fluorides Bearing α,β-Unsaturated Amides
Kamitani, Miharu,Tobisu, Mamoru,Yasui, Kosuke
supporting information, p. 14157 - 14161 (2019/08/30)
Concerted nucleophilic aromatic substitution (CSNAr) has emerged as a powerful mechanistic manifold, in which nucleophilic aromatic substitution can proceed in one step without the need to form a Meisenheimer intermediate. However, all of the CSNAr reactions reported thus far require a stoichiometric strong base or activating reagent, and no catalytic variants have yet been reported. Herein, we report an N-heterocyclic carbene (NHC)-catalyzed intramolecular cyclization of acrylamides that contain a 2-fluorophenyl group on the nitrogen through a CSNAr reaction. By using this catalytic method, it is possible to synthesize an array of quinolin-2-one derivatives, which are common structural motifs in pharmaceuticals and organic materials. DFT calculations unambiguously revealed that this reaction proceeds through the concerted nucleophilic aromatic substitution of aryl fluorides, in which a stereoelectronic σ (Cipso-Cβ)→ σ*(Cipso-F) interaction critically contributes to the stabilization of the transition state for the cyclization.
NOVEL SULFONAMIDE COMPOUNDS
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Page/Page column 21, (2008/06/13)
The invention relates to sulfonamide compounds of formula (I), where A, B, R3 and R4 are as defined in the claims, and their use as orexin receptor antagonists in the prevention and treatment of eating and drinking disorders, all types of sleep disorders, all kinds of cognitive dysfunctions in the healthy population and psychiatric and neurologic disorders. Formula (I).