- Molecular and crystal structures, vibrational studies and quantum chemical calculations of 3 and 5-nitroderivatives of 2-amino-4-methylpyridine
-
The crystal structures of 2-amino-4-methyl-3-nitropyridine (I), 2-amino-4-methyl-3,5-dinitropyridine (II) and 2-amino-4-methyl-5-nitropyridine (III) have been determined. The compounds crystallize in the monoclinic P2 1/n, triclinic P-1 and monoclinic C2/c space groups, respectively. These structures are stabilized by a combination of N-H···N and N-H···O hydrogen bonds and exhibit layered arrangement with a dimeric N-H···N motif in which the molecular units are related by inversion centre. The molecular structures of the studied compounds have been determined using the DFT B3LYP/6-311G(2d,2p) approach and compared to those derived from X-ray studies. The IR and Raman wavenumbers have been calculated from the optimized geometry of monomers and dimers formed in the unit cell and compared to the experimental values obtained from the spectra.
- Bryndal,Kucharska,Sasiadek,Wandas,Lis,Lorenc,Hanuza
-
-
Read Online
- Preparation method of 2-amino substituted six-membered nitrogen-containing heterocycle complex
-
The invention discloses a preparation method of a 2-amino substituted six-membered nitrogen-containing heterocycle complex. The preparation method comprises the following steps: mix 2-fluorine substituted six-membered nitrogen-containing heterocycle complex and amidine hydrochloride salt compound, and then react under the action of a alkaline substance to obtain a 2-amino substituted six-memberednitrogen-containing heterocycle complex. Preferably, the 2-amino substituted six-membered nitrogen-containing heterocycle complex is a 2-amino pyridine compound, a 2-aminopyrimidine compound or a 2-aminopyrazine compound. Compared with the prior art, the method has the advantages of simple synthesis conditions, less reaction steps, mild reaction conditions, low cost of the catalyst used, less waste discharge and good functional group tolerance.
- -
-
Paragraph 0049; 0050
(2019/02/08)
-
- Transition-metal-free access to 2-aminopyridine derivatives from 2-fluoropyridine and acetamidine hydrochloride
-
Under catalyst-free conditions, an efficient method for the synthesis of 2-aminopyridine derivatives through the nucleophilic substitution and hydrolysis of 2-fluoropyridine and acetamidine hydrochloride has been developed. This amination uses inexpensive acetamidine hydrochloride as the ammonia source and has the advantages of a high yield, high chemoselectivity and wide substrate adaptability. The results suggest that other N-heterocycles containing fluorine substituents can also complete the reaction via these reaction conditions and yield the target products.
- Li, Yibiao,Huang, Shuo,Liao, Chunshu,Shao, Yan,Chen, Lu
-
supporting information
p. 7564 - 7567
(2018/11/02)
-
- Ethanol compound used as FGFR inhibitor
-
The invention discloses an ethanol compound used as a FGFR inhibitor. The invention provides the compound as shown in a formula I which is described in the specification or a pharmaceutically acceptable salt thereof, a preparation method for the compound and application of the compound as a medicine to treatment of cancers.
- -
-
Paragraph 0044
(2017/03/17)
-
- Theoretical and experimental NMR data of 3,5-dinitro-2-(2-phenylhydrazinyl) pyridine and of its 4- and 6-methyl derivatives
-
3,5-Dinitro-2-(2-phenylhydrazinyl)pyridine and its methyl derivatives: 4-methyl-3,5-dinitro-2-(2-phenylhydrazinyl)pyridine and 6-methyl-3,5-dinitro-2- (2-phenylhydrazinyl)pyridine were synthesized and characterized by 1H NMR and 13C NMR. Calculations were also performed where the above molecules were optimized using the methods of density functional theory (DFT) with 6-31G(d,p) and 6-311G(d,p) basis sets. For all molecules studied, the lowest energy was obtained using the 6-311G(d,p) basis set. The GIAO/DFT (Gauge Invariant Atomic Orbitals/Density Functional Theory) calculations on the 6-311G and 6-311++G and 6-311G* basis sets were carried out to determine proton and carbon chemical shifts and to find they were close to the experimental values. It has been also found that intramolecular hydrogen bonding exists between hydrogen atom (in 2-NH group) and oxygen atom (pyridine-3-NO2). Moreover, resonances between pyridine ring and electron withdrawing 3-nitro group as well between that ring and the lone electron pair of NH group favor a co-planarity of the structure; this means a chelate ring created by above-mentioned intramolecular hydrogen bond is almost co-planar with pyridine ring.
- Wandas,Talik
-
-
- BICYCLIC HETEROARYL COMPOUNDS AS GPR119 RECEPTOR AGONISTS
-
The present invention provides a new class of bicyclic heteroaryl compounds represented by Formula (I), pharmaceutical compositions containing these compounds, and their use for modulating the activity of GPR119 in the treatment of metabolic disorders and complications thereof, as well as methods for the treatment of the metabolic disorders and complications thereof.
- -
-
Page/Page column 43
(2012/08/27)
-
- Synthesis of some fluorine-containing pyridinealdoximes of potential use for the treatment of organophosphorus nerve-agent poisoning
-
Fluoroheterocyclic aldoximes were screened as therapeutic agents for the treatment of anticholinesterase poisoning. 2-Fluoropyridine-3- and -6-aldoxime, and 3-fluoropyridine-2- and -4-aldoxime, were synthesised. Attempts to obtain 3,5,6-trifluoropyridine-2,4-bis(aldoxime) and -2-aldoxime, however, proved unsuccessful. Pentafluorobenzaldoxime was prepared by oximation of pentafluorobenzaldehyde. Acid dissociation constants (pKa) and second-order rate constants (kox-) of the fluorinated pyridinealdoximes towards sarin were measured. 2,3,5,6-Tetrafluoropyridine-4- aldoxime had the best profile: its kox- approached that of the therapeutic oxime P2S (310 vs. 120 l mol-1 min-1), but its higher pKa (9.1 vs. 7.8) fell short of the target figure of 8 required for reactivation of inhibited acetylcholinesterase in vivo. N-alkylation of the fluorinated pyridine-aldoximes may reduce their pK a nearer to 8 and enhance their therapeutic potential. Crown Copyright
- Timperley, Christopher M.,Banks, R. Eric,Young, Ian M.,Haszeldine, Robert N.
-
scheme or table
p. 541 - 547
(2011/09/15)
-
- THE NITROPYRIDINYL ETHYLENEIMINE COMPOUND, THE PHARMACEUTICAL COMPOSITION CONTAINING IT, THE PREPARATION METHOD AND USE THEREOF
-
The present invention discloses a nitropyridinyl ethyleneimine compound as shown in the formula I and a preparation method of the same, as well as use of the compound in manufacture of a prodrug and in manufacture of a drug for treating a tumor.
- -
-
Page/Page column 12-13
(2011/10/10)
-
- An alternate route to 2-amino-3-nitro-5-bromo-4-picoline: Regioselective pyridine synthesis via 2-nitramino-picoline intermediate
-
The 2-nitramino functionality in 2-nitramino-4-picoline was successfully exploited not only as a protecting group but also as a directional handle to afford an efficient, atom-economic, and regioselective synthesis of 2-amino-5-bromo-3-nitro-4-picoline (4), a precursor for a drug candidate in development.
- Bhattacharya, Apurba,Purohit, Vikram C.,Deshpande, Prashant,Pullockaran, Annie,Grosso, John A.,DiMarco, John D.,Gougoutas, Jack Z.
-
p. 885 - 888
(2012/12/30)
-
- 6-AZAINDOLE COMPOUND
-
A compound represented by the formula (I) wherein R1, R2, R3 and R6 are the same or different and each is a hydrogen atom or a substituent; one of R4 and R5 is a hydrogen atom and the other is a group represented by the formula: -C(=X)-R7 wherein X is N-O-R8 or N-NH-R9 wherein R8 and R9 are the same or different and each is a hydrogen atom or a group bonded via a carbon atom; and R7 is a hydrogen atom or a substituent, and the like and a salt thereof have a superior IκB kinase inhibitory activity, and useful as pharmaceutical agents such as agents for preventing or treating diabetes and the like.
- -
-
Page/Page column 176
(2008/06/13)
-
- Selective vicarious nucleophilic amination of 3-nitropyridines
-
Nine 3-nitropyridine compounds and 4-nitroisoquinoline have been aminated in the 6-position (for 4-nitroisoquinoline in the 1-position) by vicarious nucleophilic substitution reactions. Two amination reagents were used, hydroxylamine and 4-amino-1,2,4-triazole. The yields were from moderate to good. Use of hydroxylamine gave an easy work-up procedure by which almost pure product was obtained directly, but 4-amino-1,2,4-triazole gave better yields of the aminated product for some of the substrates. By this, a general method for the preparation of 3- or 4-substituted-2-amino-5-nitropyridines was obtained.
- Bakke, Jan M.,Svensen, Harald,Trevisan, Raffaela
-
p. 376 - 378
(2007/10/03)
-
- SYNTHESES WITH AROMATIC NITRAMINES, VI SUBSTITUENT EFFECT IN THE PHOTOLYTIC REARRANGEMENT OF NITRAMINOPYRIDINES
-
All isomeric ring-substituted methyl-2-nitraminopyridines, both 3-nitro- and 5-nitro-2-nitraminopyridines, 5-chloro- and 3-carboxy-2-nitraminopyridines, as well as 3,5-dibromo-2-nitraminopyridine were photolyzed in methanol by irradiation with a low-pressure mercury lamp (253.7 nm).Preference was generally noted for the migration of the side-chain nitro group to the vicinal β-position. 3,5-Dibromo-2-nitraminopyridine gave both 2-amino-3,5-dibromopyridine and 3,5-dibromopyridine-2-one.The ratio of the preparative and quantum yields of the two products were 2.5 and 3.0, respectively.
- Sepiol, Jadwiga,Tomasik, Piotr
-
p. 333 - 338
(2007/10/02)
-
- The Effect of Acid Concentration on the Pyridine Nitramine Rearrangement: an N.M.R. Study
-
The rearrangement of 2- and 4-nitraminopyridines in 70-95percent sulfuric acid has been investigated by n.m.r.Ring nitration is favoured by conditions leading to initial dissociation of the nitramine, and the results provide no support for an intramolecul
- Deady, Leslie W.,Korytsky, Olga L.
-
p. 1159 - 1166
(2007/10/02)
-
- Kinetic Studies of the Mechanism of the Nitraminopyridine Rearrangement
-
Rate data are reported for the rearrangement, in 92percent sulfuric acid at 30 deg C, of a series of 4-X-2-nitraminopyridines (X=H, Me, Br, Cl, MeO, CO2H) and of 4-methyl-2-nitramino(3-D)-pyridine.Values of pKa for second protonation of the corresponding pyridin-2-amines were also measured and rate constants for nitration of the monoprotonated pyridinamines were thereby calculated.The results suggest that the rate-determining step occurs prior to formation of the appropriate 3- and 5-nitro ? complexes.The nature of this step is not clear, however, and a key role for the nitramine itself is not proven by the current evidence
- Deady, Leslie W.,Korytsky, Olga L.
-
p. 2035 - 2040
(2007/10/02)
-