16096-13-2Relevant articles and documents
Preparation method of ortho-alkoxy substituted pyridine compound
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Paragraph 0059-0060, (2021/09/08)
The invention provides a preparation method of an ortho-alkoxy substituted pyridine compound, the preparation method comprises the following step: reacting an ortho-amino substituted pyridine compound with an ortho-formate compound in the presence of a nitrite compound to generate the ortho-alkoxy substituted pyridine compound. The method has the advantages of high efficiency, low cost, environmental protection and the like.
Diazotization of Aminopyridines in the Presence of Camphorsulfonic Acid. Synthesis and Some Properties of Pyridinyl Camphorsulfonates
Erin, K. D.,Filimonov, V. D.,Krasnokutskaya, E. A.,Sanzhiev, A. N.
, p. 922 - 929 (2021/07/22)
Abstract: Diazotization of 2-, 3-, and 4-aminopyridines in the presence of both racemic camphor-10-sulfonic acid and its pure enantiomers led to the formation of the corresponding pyridyl camphorsulfonates in moderate yields. Pyridyl camphorsulonates were
Antimycobacterial cycloartane derivatives from the roots of Trichilia welwistchii C. DC (Meliaceae)
Tsamo, Armelle Tontsa,Fodja Saah, Edwige P.,Langat, Moses K.,Mkounga, Pierre,Kamdem Waffo, Alain Fran?ois,Nkengfack, Augustin Ephrem
, p. 475 - 480 (2021/08/16)
Chemical investigation of the roots of Trichilia welwitschii yielded a cycloartane type terpenoid 28,29-bis-norcycloart-24-en-3β,4α,6α-triol (1), isolated as pure compound for the first time, three coumarins and three sterols. New cycloartane derivatives (1a) and (1b+1c) were obtained by hemi-synthetic reaction of compound 1. The structures of 1a-c were established by spectroscopic methods including 1D and 2D-NMR analysis, HR-EIMS, chemical transformations and by comparison of these data with those of related compounds. Evaluated for their antimycobacterial potential, compound 1 and 1b+1c were determined to show significant activities against Mycobacterium tuberculosis MIC values of 6.25 μg mL-1 while compound 1a displayed weak activity showing MIC > 100 μg mL-1. Compounds 2-4 displayed moderate activity with MIC values range from 12.5 to 50 μg mL-1.
Stabilised 2,3-pyridyne reactive intermediates of exceptional dienophilicity
Connon, Stephen J.,Hegarty, Anthony F.
, p. 3477 - 3483 (2007/10/03)
The enhanced dienophilicity of 4-methoxy, 4-aryloxy and 4-thiophenoxy analogues 6-9 of 2,3-pyridyne (2) relative to 2 itself is reported. The regioselective lithiation of 4-alkoxy-(22, 23 and 25) and 4-thiophenoxy-2- chloropyridme (24) at low temperatures, followed by elimination of lithium chloride affords 4-alkoxy- and 4-thiophenoxypyridynes, which can be trapped in situ in a [4+2] cycloaddition reaction with furan to give endoxides 28-31 in moderate to good yields (25-58%). In contrast, precursors with a hydrogen (18) or methyl (12) substituent at C-4 give no evidence for pyridyne formation under these conditions. Attempts to generate 6-isopropoxy-2,3-pyridyne (10) from the low-temperature lithiation of 2-chloro-6-isopropoxypyridine were unsuccessful due to the instability of the 2-chloro-6-isopropoxy-5-lithiopyridine. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
Highly efficient synthesis of o-(2,4-dinitrophenyl)hydroxylamine. Application to the synthesis of substituted N-benzoyliminopyridinium ylides
Legault, Claude,Charette, Andre B.
, p. 7119 - 7122 (2007/10/03)
An efficient two-step synthesis of O-(2,4-dinitrophenyl)hydroxylamine is described along with a comparison of its aminating efficiency with O-mesitylenesulfonylhydroxylamine (MSH). It was used in an expedient N-amination/benzoylation procedure involving various substituted pyridines, leading to polysubstituted N-benzoyliminopyridinium ylides, and the scope of its amination power was studied.
The Mechanisms of Thermal Eliminations. Part 11. Rate Data for Pyrolysis of 2-Alkoxypyridines to 2-Pyridone, and of 2-Ethoxypicolines to 2-Picolones: Nature and Polarity of the Transition State
Al-Awadi, Nouria,Ballam, John,Hemblade, Paul R.,Taylor, Roger
, p. 1175 - 1178 (2007/10/02)
The rates of thermal elimination of 2-ethoxy-, 2-isopropoxy-, 2-t-butoxy-pyridine to 2-pyridone and the corresponding alkene, and of the 2-ethoxy derivatives of 3-, 4-, 5-, and 6-methylpyridines to ethylene and the corresponding 2-picolines have been measured over at least 50 deg for each compound, between 585.1 and 721.1 K.The respective log (A/s-1) and Ea/kJ mol-1 values for the former three compounds are 12.20, 196.5; 12.68, 187.6; and 12.33, 161.0, and these are similar to those for the corresponding acetates.The relative rates of the first-order unimolecular decomposition at 600 K are: Et(1.0), Pri(18.0), But(1645) compared with 1.0:28.8:3316 for the acetates.The polarity of the transition state is thus less than for ester elimination.The difference in the rate ratios k(Pri)/k(Et) for alkoxypyridine and acetate pyrolyses is greater than the difference in the k(But)/k(Pri) ratios and is interpreted in terms of the difference in polarity of the transition states for primary, secondary, and tertiary elimination.Methyl substituents in the 3-, 4-, 5-, and 6-positions of the pyridine ring change the rate at 600 K by factors of 1.57, 1.02, 0.74, and 1.08, respectively.These show the decomposition does not take place via N-alkylpyridone tautomers, and that the reaction is, like ester pyrolysis, sterically accelerated.