- Tetracarbonylmolybdenum complexes of 2-(phenylazo) pyridine ligands. Correlations of molybdenum-95 chemical shifts with electronic, infrared, and electrochemical properties
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The complexes cis-Mo(CO)4(X-2-(phenylazo)pyridine) (X = 4-CH3O, 4-CH3, H, 4-Cl, 5-Br, 5-CF3, 6-CH3) and cis-Mo(CO)4(2-(2-CH3-phenylazo)pyridine) have been synthesized and characterized by cyclic voltammetry, by visible and infrared spectroscopy, and by 1H, 13C, and 95Mo NMR spectroscopy. The 95Mo chemical shift correlates with the lowest energy electronic transition, with the sum of the carbonyl stretching frequencies, with the first oxidation potential, and with Hammett σ parameters for the pyridyl substituents. The failure of the complexes cis-Mo(CO)4(6-CH3-2-(phenylazo)pyridine) and cis-Mo(CO)4(2-(2-CH3-phenylazo)pyridine) to fit some of the correlations is attributed to steric or electronic effects. The effect of a substituent on the pyridyl ring of 2-(phenylazo)pyridine appears to be entirely an inductive one operating through the σ bonding. It is suggested that the 2-(phenylazo)pyridines might be appropriately viewed as ligands whose strong π-acceptor ability resides with the azo group, while the pyridyl group acts primarily as a pyridine whose basicity has been decreased by the strong electron-withdrawing 2-phenylazo substituent.
- Ackermann, Martin N.,Fairbrother, William G.,Amin, Neelim S.,Deodene, Charles J.,Lamborg, Carl M.,Martin, Paul T.
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- A convenient synthetic route to substituted pyrrolo[2,3-b]pyridines via a novel ethylene-bridged compound
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A convenient synthetic route to 4-substituted pyrrolo[2,3-b]pyridines is presented. The novel ethylene bridged compound 1,2-bis(4-azidopyrrolo[2,3-b]pyridinyl)ethene was prepared and further derivatized. The novel synthesis was applied in the preparation of 3-cyano-4-hydroxypyrrolo[2,3-b]pyridine.
- Wilding, Birgit,Vidovic, Carina,Klempier, Norbert
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- Ruthenium-Catalyzed Reductive Arylation of N-(2-Pyridinyl)amides with Isopropanol and Arylboronate Esters
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A new three-component reductive arylation of amides with stable reactants (iPrOH and arylboronate esters), making use of a 2-pyridinyl (Py) directing group, is described. The N-Py-amide substrates are readily prepared from carboxylic acids and PyNH2, and the resulting N-Py-1-arylalkanamine reaction products are easily transformed into the corresponding chlorides by substitution of the HN-Py group with HCl. The 1-aryl-1-chloroalkane products allow substitution and cross-coupling reactions. Therefore, a general protocol for the transformation of carboxylic acids into a variety of functionalities is obtained. The Py-NH2 by-product can be recycled.
- Ronson, Thomas O.,Renders, Evelien,Van Steijvoort, Ben F.,Wang, Xubin,Wybon, Clarence C. D.,Prokopcová, Hana,Meerpoel, Lieven,Maes, Bert U. W.
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supporting information
p. 482 - 487
(2019/01/04)
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- BCR-ABL TYROSINE-KINASE LIGANDS CAPABLE OF DIMERIZING IN AN AQUEOUS SOLUTION, AND METHODS OF USING SAME
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Described herein are monomers capable of forming a biologically useful multimer when in contact with one, two, three or more other monomers in an aqueous media. In one aspect, such monomers may be capable of binding to another monomer in an aqueous media (e.g. invivo) to form a multimer (e.g. a dimer). Contemplated monomers may include a ligand moiety, a linker element, and a connector element that joins the ligand moiety and the linker element. In an aqueous media, such contemplated monomers may join together via each linker element and may thus be capable of modulating one or more biomolecules substantially simultaneously, e.g., modulate two or more binding sites on a Bcr-Abl tyrosine kinase.
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Paragraph 00592; 00603; 00604
(2015/07/23)
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- AMINO-PYRIDINE-CONTAINING SPLEEN TYROSINE KINASE (SYK) INHIBITORS
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The invention provides certain amino-pyridine-containing compounds of the Formula (I) (I) or pharmaceutically acceptable salts thereof, wherein R3, R4, R5, R6, and the subscript n are as defined herein. The invention also provides pharmaceutical compositions comprising such compounds, and methods of using the compounds for treating diseases or conditions mediated by Spleen Tyrosine Kinase (Syk) kinase.
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Paragraph 00165
(2014/05/24)
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- Consecutive gold(I)-catalyzed cyclization reactions of o -(buta-1,3-diyn-1-yl-)-substituted N-aryl ureas: A one-pot synthesis of pyrimido[1,6- a ]indol-1(2 H)-ones and related systems
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Treatment of readily available o-(buta-1,3-diyn-1-yl-)-substituted N-aryl ureas such as 1 with the Au(I)-catalyst 11 affords, via a twofold cyclization process, the isomeric pyrimido[1,6-a]indol-1(2H)-one 3 in good yield.
- Sharp, Phillip P.,Banwell, Martin G.,Renner, Jens,Lohmann, Klaas,Willis, Anthony C.
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supporting information
p. 2616 - 2619
(2013/07/11)
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- Synthesis of C8-N9 annulated purines by iron-catalyzed C-H amination
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Purine and simple: A short synthesis for substituted annulated purine derivatives based on an Fe-catalyzed direct amination reaction using oxygen as oxidant was developed (see scheme). Interestingly, iron proved to be superior to copper catalysis. Copyright
- Maes, Jens,Rauws, Tom R. M.,Maes, Bert U. W.
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supporting information
p. 9137 - 9141
(2013/07/26)
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- Ligandless copper-catalyzed coupling of heteroaryl bromides with gaseous ammonia
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A range of different N- and S-containing heterocyclic bromides can be efficiently coupled with gaseous ammonia in the presence of copper(II) acetylacetonate [Cu(acac)2] as catalyst and in the absence of additional ligands. Unstable aminothiophenes and aminobenzothiophenes can be further reacted in situ to afford functionalized derivatives. Copyright
- Fantasia, Serena,Windisch, Johannes,Scalone, Michelangelo
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supporting information
p. 627 - 631
(2013/04/11)
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- AMINO-PYRIDINE-CONTAINING SPLEEN TYROSINE KINASE (SYK) INHIBITORS
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The invention provides certain amino-pyridine-containing compounds of the Formula (I) or pharmaceutically acceptable salts thereof, wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, and n are as defined herein. The invention also provides pharmaceutical compositions comprising such compounds, and methods of using the compounds for treating diseases or conditions mediated by Spleen Tyrosine Kinase (Syk) kinase.
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Page/Page column 50-51
(2012/11/14)
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- COMPOUNDS OF ESTROGEN-RELATED RECEPTOR MODULATORS AND THE USES THEREOF
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The compounds according to formula (I), their pharmaceutically acceptable acid or base addition salts, and the uses thereof. These compounds and their pharmaceutically acceptable acid or base addition salts can be used for preparing medicaments for modula
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- Scaffold-hopping strategy: Synthesis and biological evaluation of 5,6-fused bicyclic heteroaromatics to identify orally bioavailable anticancer agents
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Utilizing scaffold-hopping drug-design strategy, we sought to identify a backup drug candidate for BPR0L075 (1), an indole-based anticancer agent. For this purpose, 5,6-fused bicyclic heteroaromatic scaffolds were designed and synthesized through shufflin
- Tung, Yen-Shih,Coumar, Mohane Selvaraj,Wu, Yu-Shan,Shiao, Hui-Yi,Chang, Jang-Yang,Liou, Jing-Ping,Shukla, Paritosh,Chang, Chun-Wei,Chang, Chi-Yen,Kuo, Ching-Chuan,Yeh, Teng-Kuang,Lin, Chin-Yu,Wu, Jian-Sung,Wu, Su-Ying,Liao, Chun-Chen,Hsieh, Hsing-Pang
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p. 3076 - 3080
(2011/06/25)
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- A general and efficient 2-amination of pyridines and quinolines
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(Chemical Equation Presented) Pyridine N-oxides were converted to 2-aminopyridines in a one-pot fashion using Ts2O-t-BuNH2 followed by in situ deprotection with TFA. The amination proceeded in high yields, excellent 2-/4-selectivity, and with good functional group compatibility. 2-Amino (iso)quinolines were also obtained in the same manner. Combined with the simple oxidation of pyridines to pyridine N-oxides, this method provides a general and efficient way for amination of 2-unsubstituted pyridines.
- Yin, Jingjun,Xiang, Bangping,Huffman, Mark A.,Raab, Conrad E.,Davies, Ian W.
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p. 4554 - 4557
(2008/02/04)
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- Cyclic ureas as ortho directing substituents
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Six-membered cyclic ureas are shown to have a weak ortho directing ability when linked through nitrogen to benzene and pyridine rings.
- Meigh,Alvarez,Joule
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p. 2012 - 2021
(2007/10/03)
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- Substituted 2-aminopyridines as inhibitors of nitric oxide synthase
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Substituted 2-aminopyridine compounds of Formula (I) and pharmaceutically acceptable salts which have been found useful in the treatment of nitric oxide synthase mediated diseases and disorders. STR1
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- Substituent Effects on the Isomer Ratios in the Rearrangement of Some 2- and 4-Nitraminopyridines
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The preparation, and rearrangement in 92percent sulfuric acid, of 4-X-2-nitramino- (1), 2-X-4-nitramino- (2), and 6-X-2-nitramino-pyridines (3) is reported (X=H,Me,MeO,Br,Cl,CO2H).The product isomer ratios can be explained by differential electronic stabilization of the appropriate ? complexes for aromatic nitration and steric effects seem relatively unimportant.Deuteration had no effect on the product distribution
- Deady, Leslie W.,Korytsky, Olga L.,Rowe, Jeffrey E.
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p. 2025 - 2034
(2007/10/02)
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- Kinetics and Mechanism of the Reaction of Pyridinamine 1-Oxides with Acetylating Agents in Water and Aprotic Solvents
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Pyridin-2-amine 1-oxides react with acetic anhydride in dioxan and with p-nitrophenyl acetate in water by rate-determining O-acetylation followed by rapid intramolecular rearrangement to give the amide.The rearrangement is so favoured that no hydrolysis of the intermediate was detected in the aqueous solvent.This behaviour in aprotic solvents contrasts with that of pyridin-2-amine, previously shown to undergo acetylation directly at the amino group.Acetylation of pyridin-4-amine 1-oxide, with acetic anhydride in acetone, occurs by way of an analogous O-acetyl intermediate which reacts slowly with a second molecule of amine 1-oxide.Pyridin-4-amine reacts in the same manner at a surprisingly similar rate.In water, both compounds catalyse the hydrolysis of p-nitrophenyl acetate, with the amine 1-oxide being very much less efficient.
- Deady, Leslie W.,Stanborough, Mark S.
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p. 1841 - 1849
(2007/10/02)
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- Studies on 1,3-Benzoxazines. I. Synthesis of Primary 2-Amino-pyridines via the Reaction of Imidoyl Chlorides of 1,3-Benzoxazines with Pyridine N-Oxides
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A new synthetic method for primary 2-aminopyridine derivatives is described.Treatment of the imidoyl chlorides of 1,3-benzoxazines (1a-i) with pyridine N-oxides resulted in the introduction of an oxazine moiety into the α-position of the pyridine ring through rearrangement of the initially formed reaction adduct.Acid hydrolysis of the rearrangement products afforded 2-aminopyridine derivatives in excellent yields.When methoxypyridine N-oxides were used, products of a different type (10 and 14) were obtained.
- Wachi, Kazuyuki,Terada, Atsusuke
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p. 465 - 472
(2007/10/02)
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