154669-56-4Relevant academic research and scientific papers
PHENETHYL SUBSTITUTED IMIDAZO[4,5-C]QUINOLINE COMPOUNDS WITH AN N-1 BRANCHED GROUP
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Page/Page column 35, (2020/12/30)
Imidazo[4,5-c]quinoline compounds having a substituent that is attached at the N-1 position by a branched group, single enantiomers of the compounds, pharmaceutical compositions containing the compounds, and methods of making the compounds are disclosed.
Staudinger/aza-Wittig reaction to access Nβ-protected amino alkyl isothiocyanates
Santhosh,Durgamma,Shekharappa,Sureshbabu, Vommina V.
, p. 4874 - 4880 (2018/07/15)
A unified approach to access Nβ-protected amino alkyl isothiocyanates using Nβ-protected amino alkyl azides through a general strategy of Staudinger/aza-Wittig reaction is described. The type of protocol used to access isothiocyanates depends on the availability of precursors and also, especially in the amino acid chemistry, on the behavior of other labile groups towards the reagents used in the protocols; fortunately, we were not concerned about both these factors as precursor-azides were prepared easily by standard protocols, and the present protocol can pave the way for accessing title compounds without affecting Boc, Cbz and Fmoc protecting groups, and benzyl and tertiary butyl groups in the side chains. The present strategy eliminates the need for the use of amines to obtain title compounds and thus, this method is step-economical; additional advantages include retention of chirality, convenient handling and easy purification. A few hitherto unreported compounds were also prepared, and all final compounds were completely characterized by IR, mass, optical rotation, and 1H and 13C NMR studies.
Hydrodehalogenation of alkyl iodides with base-mediated hydrogenation and catalytic transfer hydrogenation: Application to the asymmetric synthesis of N-protected α-methylamines
Mandal, Pijus K.,Birtwistle, J. Sanderson,McMurray, John S.
, p. 8422 - 8427 (2015/03/18)
We report a very mild synthesis of N-protected α-methylamines from the corresponding amino acids. Carboxyl groups of amino acids are reduced to iodomethyl groups via hydroxymethyl intermediates. Reductive deiodination to methyl groups is achieved by hydrogenation or catalytic transfer hydrogenation under alkaline conditions. Basic hydrodehalogenation is selective for the iodomethyl group over hydrogenolysis-labile protecting groups, such as benzyloxycarbonyl, benzyl ester, benzyl ether, and 9-fluorenyloxymethyl, thus allowing the conversion of virtually any protected amino acid into the corresponding N-protected α-methylamine.
The diastereoselective alkylation of arenesulfenate anions using homochiral electrophiles
Soederman, Stefan C.,Schwan, Adrian L.
supporting information; experimental part, p. 4192 - 4195 (2011/10/08)
A series of Boc-protected β-amino sulfoxides were prepared by the reaction of arenesulfenate anions with chiral Boc-protected β-amino iodides. The stereoselective substitution reaction is believed to arise through precoordination of the sulfenate counteri
PROP-2-YN-1-AMINE INHIBITORS OF MONOAMINE OXIDASE TYPE B
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Page/Page column 10, (2010/12/29)
The present invention relates to new prop-2-yn-1-amine inhibitors of monoamine oxidase type B activity, pharmaceutical compositions thereof, and methods of use thereof.
Synthesis of thioureido-linked peptidomimetics, glycosylated amino acids, and neoglycoconjugates using bis(benzotriazolyl)methanethione as thioacylating agent
Sureshbabu, Vommina V.,Chennakrishnareddy, Gundala,Hemantha, Hosahalli P.
body text, p. 715 - 720 (2010/06/14)
A practical synthesis of thiourea-linked peptidomimetics, glycosylated amino acids, and neoglycoconjugates is described employing bis(benzotriazolyl) methanethione as thiocarbonylating reagent. The entire protocol is mild, efficient, high-yielding, and free from hazardous reagents. All the intermediates and products have been isolated and fully characterized by 1H NMR, 13C NMR, and mass spectrometry. Georg Thieme Verlag Stuttgart ? New York.
One-pot synthesis of orthogonally protected enantiopure S-(aminoalkyl)-cysteine derivatives
Bolognese, Adele,Fierro, Olga,Guarino, Daniela,Longobardo, Luigi,Caputo, Romualdo
, p. 169 - 173 (2007/10/03)
The general synthesis of a new class of non-natural diamino acids, 2-amino-3-[(2′-aminoalkyl)thio]propanoic acids or S-(aminoalkyl)cysteines, is reported. Under the conditions devised, enantiopure N-Boc-protected β-iodoamines, readily generated from proteinogenic α-amino acids, are treated with L-cysteine ethyl ester hydrochloride, using Cs2CO 3 as a base. The S-alkylation products, obtained in high yields (96-98 %) and without any detectable traces of accompanying byproducts, are hydrolysed to yield the free carboxyl group. An orthogonal protection is then introduced on the free amino group by treatment with Fmoc-OSu under standard conditions. The inclusion of one of these orthogonally protected diamino acids in a solid-phase growing pentapeptide is also reported. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
Stereoselective synthesis of 2-alkenylaziridines and 2-alkenylazetidines by palladium-catalyzed intramolecular amination of α- and β-amino allenes
Ohno,Anzai,Toda,Ohishi,Fujii,Tanaka,Takemoto,Ibuka
, p. 4904 - 4914 (2007/10/03)
Whereas palladium-catalyzed reaction of N-arylsulfonyl-α-amino allenes with an aryl iodide (4 equiv) in the presence of potassium carbonate (4 equiv) in DMF at around 70 °C affords the corresponding 3-pyrroline derivatives, the reaction in refluxing 1,4-dioxane under otherwise identical conditions yields exclusively or most predominantly the corresponding 2-alkenylaziridines bearing an aryl group on the double bond. Similarly, N-arylsulfonyl-β-amino allenes can be also cyclized into the corresponding alkenylazetidines bearing a 2,4-cis-configuration under palladium-catalyzed cyclization conditions in DMF.
Efficient synthesis of protected β-phenylethylamines, enantiomerically pure protected β-phenyl-α-benzylethylamines and β-phenyl-α-isopropylethylamines using organozinc chemistry
Hunter, Christopher,Jackson, Richard F. W.,Rami, Harshad K.
, p. 219 - 223 (2007/10/03)
The β-aminoalkylzinc reagents 9a, 10 and 11 have been efficiently prepared using DMF as a solvent. Palladium-catalysed coupling of these reagents with substituted aryl iodides, under mild and convenient conditions, gives protected β-phenylethylamines 6 in
