13683-44-8Relevant academic research and scientific papers
Synthesis of 3-Sulfonylamino Quinolines from 1-(2-Aminophenyl) Propargyl Alcohols through a Ag(I)-Catalyzed Hydroamination, (2 + 3) Cycloaddition, and an Unusual Strain-Driven Ring Expansion
Kumar, Yalla Kiran,Kumar, Gadi Ranjith,Reddy, Thota Jagadeshwar,Sridhar, Balasubramanian,Reddy, Maddi Sridhar
, p. 2226 - 2229 (2015/05/13)
We describe herein a silver-catalyzed conversion of 1-(2-aminophenyl)-propargyl alcohols to 4-substituted 3-tosylaminoquinolines using TsN3 as an amino surrogate. Controlled reactions reveal the pathway consisting of Ag(I)-catalyzed 5-exo-dig cyclization, catalyst-free (2 + 3) cycloaddition, and ring-expansive rearrangement via nitrogen expulsion. As a support study, we show that the cyclic enamines in similar conditions produce amidines via a C - C bond migration. (Chemical Equation Presented).
N-Alkylation of amines through hydrogen borrowing over a heterogeneous Cu catalyst
Santoro, Federica,Psaro, Rinaldo,Ravasio, Nicoletta,Zaccheria, Federica
, p. 2596 - 2600 (2014/01/06)
Substitution of alkylhalides for the synthesis of amines is a relevant target for synthetic chemists. Secondary amines can be obtained in a one pot-one step reaction from secondary and benzylic alcohols and aniline over a heterogeneous copper catalyst. The process does not require any additive, is intrinsically safe and produces no waste.
In vitro antifungal activity of new series of homoallylamines and related compounds with inhibitory properties of the synthesis of fungal cell wall polymers
Vargas M., Leonor Y.,Castelli, Maria V.,Kouznetsov, Vladimir V.,Urbina G., Juan M.,Lopez, Silvia N.,Sortino, Maximiliano,Enriz, Ricardo D.,Ribas, Juan C.,Zacchino, Susana
, p. 1531 - 1550 (2007/10/03)
The synthesis, in vitro antifungal evaluation and SAR studies of 101 compounds of the 4-aryl-, 4-alkyl-, 4-pyridyl or -quinolinyl-4-N-arylamino-1-butenes series and related compounds, are reported here. Active structures showed to inhibit (1,3)-β-D-glucan and mainly chitin synthases, enzymes that catalyze the synthesis of the major fungal cell wall polymers.
Synthesis of new spiro-N-heterocycles with cyclooctane fragment from N- (1-alkenylcyclooctyl)-N-aryl(benzyl) amines
Vargas, Leonor M.,Rozo, Wilson,Kouznetsov, Vladimir
, p. 785 - 796 (2007/10/03)
The homoallylic amines (6-10) derived from N-cyclooctylidenearyl (benzyl)amines and allyl- or prenylmagnesium bromides as organometallic reagents have been used for synthesis of spiro-N-heterocycles. The tetrahydrospiro[3H-2-benzazepine-3,1'-cyclooctanes] (11 and 12) have been obtained from the homoallylamines (6 and 7) under acidic conditions. The tetrahydro-1-benzazepine (15) spiroannulated with a cyclooctane moiety has been prepared by treating the homoallylic amine (9) with conc. sulfuric acid. Treatment of the homoallylmine (6) with 92% sulfuric acid in chloroform at reflux afforded tetrahydrospiro[1,2,3-oxathiazine-2,2-dioxide-4,1'- cyclooctane] (17). The latter has been converted into 1-benzyl-4- methylspiro[azetidine-2,1'-cyclooctane] (18). The homoallylamine (6) has been cyclized into the 1-benzylspiro[pyrrolidine-2,1'-cyclooctane] (19).
Reactions of Olefin Complexes with Nitrene Precursors. Synthesis of Triazoline and Aziridin Complexes of Palladium(II); Crystal and Molecular Structure of trans-Dichlorobis(11-phenyl-9,10,11-triazabicycloundec-9-ene-N9)palladium-Chloroform(1/2)
Porta, Francesca,Pizzotti, Maddalena,Monica, Gerolamo La,Finessi, Luis A.,Cenini, Sergio,et al.
, p. 2409 - 2414 (2007/10/02)
By reaction at 70 deg C of phenyl azide with a suspension of PdCl2 and cis-cyclo-octene, the complex has been isolated, and its crystal and molecular structure determined.This compound crystallizes in triclinic space group with a=9.258(2), b=10.702(3), c=11.156(2) Angstroem, α=113.94(3), β=99.60(2), γ=104.87(3) deg, and Z=1.The metal lies on a symmetry centre and the complex configuration is trans planar.The chloroform molecules are hydrogen bonded to the co-ordinated chloride ions.The reaction of phenyl azide with cis-cyclo-octene at 70 deg C in the absence of PdCl2 leads to the corresponding anil, N-cyclo-octylideneaniline, .Preformed 2> reacts with phenyl azide in cyclo-octene at 70 deg C to give .By comparison, has been synthesized from the reaction of with N-cyclo-octylideneaniline.
Azomethines, 1-Azaallyl Anions, and Metastable Secondary Enamines
Knorr, Rudolf,Weiss, Alfons,Loew, Peter,Raepple, Edith
, p. 2462 - 2489 (2007/10/02)
E/Z equilibrium constants of the ketone anils 6a-s do not depend significantly on the inductive substituent effect. 1H NMR chemical shifts used for configurational classification are also effective for assignments in comparable, isomerically almost pure azomethines 6aa-pp and may be explained by the anisotropic shift model.The 1-azaallyl anions 7 prepared by deprotonation are characterized by 1H NMR spectroscopy.Kinetic and thermodynamic control of this metallation reaction result in different preferential configurations of such anions, the methanolysis of which yields metastable sec. enamines 8 by regio- and stereospecific N-protonation.It is possible to estimate further substituent parameters λd from E/Z equilibria.
