39930-11-5Relevant articles and documents
Construction and regulation of imidazo[1,5-a]pyridines with AIE characteristics via iodine mediated Csp2?H or Csp?H amination
Zhang, Jun,She, Mengyao,Liu, Lang,Liu, Mengdi,Wang, Zhaohui,Liu, Hua,Sun, Wei,Liu, Xiaogang,Liu, Ping,Zhang, Shengyong,Li, Jianli
supporting information, p. 3083 - 3086 (2021/06/28)
The widespread applications of aggregation-induced emission luminogens (AIEgens) inspire the creation of AIEgens with novel structures and functionalities. In this work, we focused on the direct and efficient synthesis of a new type of AIEgens, imidazo[1,5-a]pyridicne derivatives, via iodine mediated cascade oxidative Csp2–H or Csp–H amination route from phenylacetylene or styrenes under mild conditions. The resulted compounds showed excellent AIE characteristics with tunable maximum emissions, attractive bioimaging performance, and potential anti-inflammatory activity, which exert broad application prospects in material, biology, medicine, and other relevant areas.
MODULATORS OF TREX1
-
Paragraph 0091, (2021/01/29)
Provided are compounds of Formula (I): and pharmaceutically acceptable salts and compositons thereof, which are useful for treating a variety of conditions associated with TREX1.
DOPAMINE D2 RECEPTOR LIGANDS
-
Page/Page column 115; 117; 135, (2016/07/05)
The present invention relates to novel dopamine D2 receptor ligands. The invention further relates to functionally-biased dopamine D2 receptor ligands and the use of these compounds for treating or preventing central nervous system and systemic disorders associated with dysregulation of dopaminergic activity.
Molecular structures of dinuclear zinc(II) complexes of chiral tridentate imine and amine ligands: Effect of ligand geometry on diastereoselectivity
Jena, Himanshu Sekhar,Manivannan, Vadivelu
, p. 210 - 219 (2013/02/22)
Racemic mixtures of Schiff bases (L1H and L2H) were reduced to respective amines (L1′H and L2′H). Compounds of composition [Zn 2(L1)2(NCO)2] (1), [Zn(L1)N3] n (2), [Zn2(L2)2(NCO)2] (3), [Zn2(L1′)2(NCO)2] (1′), [Zn 2(L1)2(N3)2]·2DMF (2′·2DMF) and [Zn2(L2′)2(NCO) 2]·DMF (3′·DMF) were synthesized using these ligands, Zn(NO3)2·6H2O and NCO - or N3- ions. Molecular structures of all six compounds have been established. Both imine and amine ligands have N 2O donor set, but coordinate, respectively, in meridional and facial fashions. First four complexes are monochelates and last two are bis-chelates. The Zn2O2 unit in 1-3 has RS combination of imine where as in 1′ has RR(SS) combinations of amine. In 2′ and 3′, zinc(II) bis-chelates have cis,cis,trans-(OP)2(N A)2(NY)2 stereochemistry and cis-(OP)2 disposition further coordinate to tetrahedral zinc. Compound 1′ exhibits 1D hydrogen-bonded polymer by enantioselective H-bonding interaction. In 2′, DMF molecules assemble RR and SS bis-chelates through N-H?O interactions.
Diastereoselectivity in dinuclear complexes of chiral tridentate ligands
Jena, Himanshu Sekhar,Manivannan, Vadivelu
experimental part, p. 154 - 162 (2012/08/07)
Using a racemic mixture of two chiral tridentate ligands 2-((1-(2-pyridyl)ethylimino)methyl)phenolate ion (L1) and 2-((phenyl(2-pyridyl) methylimino)methyl)phenolate ion (L2) and Cu(II) or Ni(II) salts, complexes having formulae [Cu(L2)(μ-1,1-NO3)]2 (1), [Cu(L2)(μ-Cl)]2 (2), [Cu2(L2)2(μ-1,2- SO4)] (3), [Cu2(L1)2(μ-1,2-SO4)] (4) and [Ni2(L2)2(OAc)(N(CN)2)(MeOH)] (5) were synthesized and characterized. Determination of molecular structures of all the five complexes confirmed the presence of a dimetallic core constructed by monochelates of the ligands. Compound 1, 2 have NO3- and Cl- bridge between two copper centers and 3-5 have phenoxo as well as SO42- (3,4) and OAc- (5) bridges. Compounds 1 and 2 have center of inversion in the dicopper core and are heterochiral. Whereas, in 3-5 center of inversion do not lie in the dimetallic core and are homochiral. Compound 1 has a rare feature of μ-1,1-NO3- bridge between two copper centers.
N-heterocyclic pyridylmethylamines: Synthesis, complexation, molecular structure, and application to asymmetric Suzuki-Miyaura and oxidative coupling reactions
Grach, Guillaume,Pieters, Gregory,Dinut, Aurelia,Terrasson, Vincent,Medimagh, Raouf,Bridoux, Alexandre,Razafimahaleo, Vanessa,Gaucher, Anne,Marque, Sylvain,Marrot, Jerome,Prim, Damien,Gil, Richard,Planas, Jose Giner,Vinas, Clara,Thomas, Isabelle,Roblin, Jean-Philippe,Troin, Yves
scheme or table, p. 4074 - 4086 (2011/10/03)
The synthesis of N,N-bidentate ligands based on a π-deficient N-heterocyclic pyridylmethylamine core is described. The preparation and characterization of the corresponding N,N-ligand-palladium complexes in solution and the solid state are illustrated. Pd complexes showed a good yield and moderate catalytic activity (up to 40% ee) in the asymmetric Suzuki-Miyaura coupling reaction, leading to methoxybinaphthyl derivatives. The combination of N,N-pyridylmethylamines with cuprous iodide revealed effective catalytic systems in oxidative naphthol derivative coupling reactions, affording the corresponding binaphthyls in high yields and with enantioselectivities of up to 61%.
Studies of the reactions of tripodal pyridine-containing ligands with Re(CO)5Br leading to rheniumtricarbonyl complexes with potential biomedical applications
Griffiths, D. Vaughan,Cheong, Yuen-Ki,Duncanson, Philip,Motevalli, Majid
experimental part, p. 10215 - 10228 (2011/12/15)
The complexes formed from the reaction of N-acylated tris-(pyridin-2-yl) methylamine (LH) with [Re(CO)5Br] depend on the structure of the ligand and the reaction conditions. Thus, while N-[1,1,1-tris-(pyridin-2-yl) methyl]acetamide coordinates through the three pyridine nitrogens to give a stable cationic complex [LHRe(CO)3Br], the analogous N-benzoyl ligand reacts under similar conditions to give a neutral complex [LRe(CO)3] with coordination through two pyridine nitrogens and a deprotonated amide. To try to explain these different outcomes, the reactions of some structurally related N-acylated [1,1-bis(pyridin-2-yl)]methylamines (L′H) with [Re(CO)5Br] have been studied and the reaction pathways identified. These studies indicate that a neutral complex [L′HRe(CO)3Br] is initially formed in which the amide portion of the ligand is uncoordinated, but that this complex under appropriate conditions then rearranges to give a cationic complex [L′HRe(CO)3]Br in which the coordinated amide nitrogen either remains protonated or is present in its imidic acid tautomeric form. Elimination of HBr from these complexes either thermally or in the presence of base then gives stable neutral complexes [L′Re(CO) 3]. The impact of the N-acyl group and any substituent at the apex of the tripodal ligands (L′′H) on the relative stabilities of intermediate complexes on the reaction pathway helps provide an explanation for the observed difference in behaviour of the N-acylated tris(pyridin-2-yl) methylamines (LH). The Royal Society of Chemistry 2011.
Coordination behavior of the (diphenylphosphanyl)[α-(2-pyridyl) benzyl]amide anion toward lithium and zinc cations
Olbert, Dirk,Goerls, Helmar,Conrad, Delf,Westerhausen, Matthias
experimental part, p. 1791 - 1797 (2010/08/13)
A two-step synthesis allows the preparation of [α-(2-pyridyl)benzyl] amine (1) in good yield. Phosphanylation in the presence of triethylamine gives (diphenylphosphanyl)[α-(2-pyridyl)benzyljamine (2), which crystallizes as a racemate in the centrosymmetric triclinic space group P1. The P-N bond lengths exhibit an average value of 168.3 pm. Lithiation of 2 with n-butyllithium yields dimeric semi(tetrahydrofuran)lithium (diphenylphosphanyl)[α-(2- pyridyl)benzyl]amide (3) with the lithium atoms in different environments. One Li atom, is in a distorted, tetrahedral environment and the other in a trigonal-planar coordination sphere with bridging amide moieties (av. Li-N 201.8, Li-O 192.4 pm). Zincation of 2 with dimethylzinc leads to the formation of dimeric methylzinc (diphenylphosphanyl)[α-(2-pyridyl)benzyr]amide (4) with a central six-membered (ZnNP)2 ring in a boat conformation (av. Zn-N 201.8, Zn-P 245.9 pm). The endocyclic P-N bonds are rather short (av. value 162.7 pm).
Synthesis of fluorescent 1,3-diarylated imidazo[1,5-α]pyridines: Oxidative condensation-cyclization of aryl-2-pyridylmethylamines and aldehydes with elemental sulfur as an oxidant
Shibahara, Fumitoshi,Sugiura, Rie,Yamaguchi, Eiji,Kitagawa, Asumi,Murai, Toshiaki
supporting information; experimental part, p. 3566 - 3568 (2009/09/05)
Oxidative condensation - cyclization of aldehydes and aryl-2- pyridylmethylamines proceeded in the presence of a stoichiometric amount of elemental sulfur as an oxidant in the absence of catalyst. The reaction gave a variety of 1,3-diarylated imidazo[l,5-a]pyridines in good to high yields. The products showed fluorescence emission in a wavelength range of 454-524 nm. The quantum yields of 1,3-diarylated imidazopyridines were greatly improved compared to those of the parent 3-monosubstituted compounds.
N-heterocyclic benzhydrylamines as new N,N-bidentate ligands in palladium complexes: Synthesis, characterization and catalytic activity
Terrasson, Vincent,Prim, Damien,Marrot, Jerome
experimental part, p. 2739 - 2745 (2009/03/12)
The synthesis of new N,N-bidentate ligands based on a π-deficient N-heterocyclic benzhydrylamine core is described. The corresponding air-stable palladium complexes are obtained in high yields and fully characterized by NMR spectroscopy and X-ray structur