6957-21-7Relevant articles and documents
CYCLOBUTYL DIHYDROQUINOLINE SULFONAMIDE COMPOUNDS
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, (2021/12/29)
The present invention provides a cyclobutyl dihydroquinoline sulfonamide compound of Formula (I), an enantiomer, diastereoisomer, atropisomer thereof, a mixture thereof, or a pharmaceutically acceptable salt thereof, that inhibits voltage-gated sodium channels, in particular Nav1.7. The compounds are useful for the treatment of diseases associated with the activity of sodium channels such as pain disorders, cough, and itch. Also provided are pharmaceutical compositions containing the compounds of the present invention. Also further provided is an atropi-selective preparation of said compounds of Formula (I), and intermediate thereof.
Nickel(II)-NΛNΛO Pincer Type Complex-Catalyzed N-alkylation of Amines with Alcohols via the Hydrogen Autotransfer Reaction
Balamurugan, Gunasekaran,Ramesh, Rengan,Malecki, Jan Grzegorz
, p. 7125 - 7135 (2020/06/08)
A highly sustainable catalytic protocol for the coupling of alcohols and amines for selective monoalkylated amines using Ni(II)-NΛNΛO pincer type complexes through the borrowing hydrogen methodology is described. An array of Ni(II) catalysts (1-3) was synthesized and characterized by various spectral and analytical methods. Furthermore, the distorted square planar geometry of the complexes (1 and 2) was substantiated with single crystal X-ray diffraction study. The inexpensive nickel-based catalytic methodology displays a broad substrate scope for the N-alkylation of aromatic and heteroaromatic amines using a diverse range of primary alcohols with excellent yields up to 97%. The present approach is environmentally benign, which liberates water as the sole byproduct. A short synthesis of drug intermediates such as mepyramine and chloropyramine illustrates the utility of the present protocol.
Ruthenium(II) complexes containing a phosphine-functionalized thiosemicarbazone ligand: Synthesis, structures and catalytic C-N bond formation reactions via N-alkylation
Ramachandran, Rangasamy,Prakash, Govindan,Selvamurugan, Sellappan,Viswanathamurthi, Periasamy,Malecki, Jan Grzegorz,Linert, Wolfgang,Gusev, Alexey
, p. 11405 - 11422 (2015/03/05)
A series of ruthenium(II) complexes incorporating a thiosemicarbazone chelate tethered with a diphenylphosphine pendant have been studied. Thus, [(PNS-Et)RuCl(CO)(PPh3)] (1), [N,S-(PNS-Et)RuH(CO)(PPh3)2] (2) and [(PNS-Et)RuCl(PPh3)] (3) were synthesized by reactions of various RuII precursors with 2-(2-(diphenylphosphino)benzylidene)-N-ethylthiosemicarbazone (PNS-Et). However, complexation of PNS-Et with an equimolar amount of [RuCl2(dmso)4] resulted in two different entities [(PNS-Et)RuCl(dmso)2] (4) and [(PNS-Et)2Ru] (5) with different structural features in a single reaction. All the RuII complexes have been characterized by analytical and various spectroscopic techniques. Compounds 1-5 were recrystallized, and the X-ray crystal structures have been reported for 1, 2 and 5. In the complexes 1 and 3-5 the ligand coordinated in a tridentate monobasic fashion by forming PNS five- and six-membered rings, whereas in 2, the ligand coordinated in a bidentate monobasic fashion by forming a strained NS four-membered ring. Furthermore, compounds 1-5 showed catalytic activity in N-alkylation of heteroaromatic amines. Notably, complexes 1-3 were found to be very efficient catalysts toward N-alkylation of a wide range of heterocyclic amines with alcohols. In the presence of a catalytic amount of 2 with 50 mol% of KOH, N1,C5-dialkylation of 4-phenylthiazol-2-amine has been investigated. Reaction of in situ generated aldehyde with amine yields the N1,C5-dialkylated products through the hydride ion transformation from alcohol. Complexes 1-3 also catalyzed a variety of coupling reactions of benzyl alcohols and sulfonamides, which were realized often with 99% isolated yields. Advantageously, only one equivalent of the primary alcohol was consumed in the process.
