5154-00-7

Usage

Uses

Used in Pharmaceutical Industry:
6-Amino-2-hydroxypyridine is used as a reactant for the synthesis of pyrido[1,2-a]pyrimidin-4-one derivatives, which are selective aldose reductase inhibitors. These derivatives exhibit antioxidant activity and are being investigated for their potential therapeutic applications in the treatment of various diseases, such as diabetes and its complications.
6-Amino-2-hydroxypyridine is also used as a reactant to synthesize carbamoyloxy derivatives of 2-substituted imidazo[1,2-a]pyridinium salts. These derivatives have been found to possess acetylcholinesterase inhibitory activity, making them potential candidates for the treatment of neurological disorders, such as Alzheimer's disease, where acetylcholinesterase inhibition is a common therapeutic approach.

Upstream product

• 141-86-6 2.6-diaminopyridine 
• 5154-00-7 6-amino-pyridin-2-ol 
• 7664-93-9 sulfuric acid 
• 7732-18-5 water 
• 142-08-5 2-Pyridone 
• 89640-67-5 6-hydroxy-pyridine-2-carboxylic acid amide 

Downstream Products

• 13575-44-5 2-Amino-5-hydroxy-thiazolo<4.5-b>pyridin 
• 33053-69-9 6-amino-2-hydroxy-pyridine-3-carboxylic acid 
• 110-86-1 pyridine 
• 1345183-69-8 2-(4-fluoro-phenyl)-5-iodo-6-{methanesulfonyl-[2-(2-nitro-benzenesulfonylamino)-ethyl]-amino}-furo[2,3-b]pyridine-3-carboxylic acid methylamide 
• 1345183-67-6 2-(4-fluoro-phenyl)-10-methanesulfonyl-5-methylene-7-(2-nitro-benzenesulfonyl)-5,6,7,8,9,10-hexahydro-1-oxa-7,10,11-triaza-cycloocta[f]indene-3-carboxylic acid methylamide 
• 824429-50-7 C₁₀H₁₄N₂O₂ 
• 511541-62-1 6-amino-5-bromo-2(1H)-pyridone 
• 770-20-7 N-(6-Oxo-1,6-dihydro-pyridin-2-yl)-acetamide 
• 511541-63-2 3-bromo-6-methoxypyridin-2-amine 

Relevant academic research and scientific papers

Ferracyclic carbamoyl complexes related to the active site of [Fe]-hydrogenase

The active site of the [Fe]-hydrogenase features an iron(ii) centre bearing cis carbonyl groups and a chelating pyridine-acyl ligand. Reproducing these unusual features in synthetic models is an intriguing challenge, which will allow both better understanding of the enzymatic system and more fundamental insight into the coordination modes of iron. By using the carbamoyl group as a surrogate for acyl, we have been able to synthesize a range of ferracyclic complexes. Initial reaction of Fe(CO)4Br2 with 2-aminopyridine yields a complex bearing a labile solvent molecule, which can be replaced by stronger donors bearing phosphorus atoms to produce a number of derivatives. Introduction of a hydroxy group using this method is unsuccessful both with a free OH group and when this is silyl-protected. In contrast, the analogous reactions starting from 2,6-diaminopyridine does allow synthesis of complexes bearing a pendant basic group.

2,6-Diamination of substituted pyridines via heterogeneous Chichibabin reaction

A series of ring substituted pyridines were selected for the sodium amide initiated heterogeneous Chichibabin amination to obtain 2,6-diaminopyridine derivatives which are important synthons for the preparation of PNP pincer ligands. The substrates were treated with an excess of sodium amide in neat mineral oil as solvent under an argon atmosphere. The reaction required temperatures of up to 215°C under vigorous stirring with an overall reaction time of 3-5 h. In the case of methyl, tert-butyl, phenyl, pyridinyl, and hydroxyl substituted pyridines the desired products were obtained in good to excellent yields (63-96%). Thus, the Chichibabin reaction provides an inexpensive and economic alternative to methodologies starting from halopyridines or pyridine N-oxides provided that the substituents are inert under the harsh reaction conditions.

The Lactam-Lactim Tautomerization of Monoamino-Substituted 2-Pyridinols in Tetrahydrofuran

MINDO/3 calculations have been performed on 3-amino-, 4-amino-, 5-amino-, and 6-amino-2-pyridinols to estimate their molecular geometries.The lactam-lactim tautomerization from amino-2-pyridone to amino-2-pyridinol was expected for 5-amino- and 6-amino-2-pyridinols from the MINDO/3 calculations.In addition, their dimer formation energies were evaluated by the CNDO/2 method.Among the four amino-2-pyridones, 6-amino-2-pyridone has the largest dimer formation energy and 3-amino-2-pyridone the smallest.Furthermore, to certify the tautomerization of 3-amino-, 5-amino-, and 6-amino-2-pyridinols the UV absorption and fluorescence spectra were measured, and compared with those of their O-methyl and nuclear N-methyl derivatives.From the UV spectral data the equilibrium constants of the lactam-lactim tautomerization were determined for 5-amino and 6-amino derivatives in tetrahydrofuran (THF) at various temperatures.The lactam form is more stable than that of the lactim; the enthalpy changes between two forms of 5-amino and 6-amino derivatives were estimated to be 7.9 and 6.3 kJ mol-1, respectively.The lactam and lactim dimers of these two derivatives were found to be easily formed in THF and ether.From the fluorescence spectral data the lactim dimer of 6-amino derivative was found to be formed in the lowest excited ?,?* singlet state.On the other hand, the 3-amino derivative exists predominantly in the lactam monomer form in both the ground and the lowest excited ?,?* singlet states.