22973-00-8Relevant academic research and scientific papers
1H NMR spectra of 1-alkyl-1,2,3,4-tetrahydro-2-oxo-3-azocine-carboxylic acid derivatives and their analogues
Somekawa,Kumamoto,Matsuo,Ueda
, p. 81 - 85 (1980)
1H NMR spectra of 1-alkyl-1,2,3,4-tetrahydro-2-oxo-3-azocinecarboxylates and -carbonitriles indicated that the geminal protons at the 1-α-position were located in noneqnivalent magnetic environments. The difference in the chemical shifts amounted to as much as 0.73 ppm in the case of methyl 1-ethyl-1,2,3,4-tetrahydro-2-oxo-3-azocinecarboxylate at 26°, and the free energy of activation for the coalescence was estimated to be larger than 23 kcal mol. The same type of nonequivalence and coalescence phenomena were also observed even with dimethyl protons at the 1-γ-position of 1-isobutyl-1,2,3,4-tetrahydro-2-oxo-3-azocinecarboxylate (ΔG≠c = 19 kcal mol). The situation was hardly affected by the reduction of the CC double bonds. The nonequivalence was not observed, however, if the substituent at the 3-position was absent. Therefore, these novel 1H NMR spectra of 1-alkyl protons in the title compounds were concluded to be due to strong coupling between the restricted rotation around N(1)-C(α) bond and inversion of the 2-oxoazocine ring which required high energy of activation.
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.
Manganese-Promoted Regioselective Direct C3-Phosphinoylation of 2-Pyridones
Chantarojsiri, Teera,Kittikool, Tanakorn,Phakdeeyothin, Kunita,Yotphan, Sirilata
supporting information, p. 3071 - 3078 (2021/07/22)
A highly efficient and regioselective manganese-induced radical oxidative direct C?P bond formation between 2-pyridones and secondary phosphine oxides was developed. The C3-selective phosphinoylation was conveniently achieved through a combination of substoichiometric manganese and persulfate oxidant under mild conditions. Various 3-phosphinoylated pyridone products can be obtained in moderate to high yields. Preliminary mechanistic studies suggest that the reaction is likely to involve a radical pathway induced by catalytically active Mn3+ species.
Metal-free regioselective direct thiolation of 2-pyridones
Phakdeeyothin, Kunita,Yotphan, Sirilata
supporting information, p. 6432 - 6440 (2019/07/09)
A highly regioselective metal-free direct C-H thiolation of 2-pyridones with disulfides or thiols has been developed. A combination of persulfate and a commercially available halide source such as LiCl, NCS or I2 enables the successful direct incorporation of a sulfide moiety into the 5-position of pyridone under mild conditions, providing a useful and convenient approach for the preparation of a diverse array of 5-thio-substituted pyridones in moderate to excellent yields.
Ir(I)-catalyzed synthesis of N-substituted pyridones from 2-alkoxypyridines via C-O bond cleavage
Pan, Shiguang,Ryu, Naoto,Shibata, Takanori
supporting information, p. 1902 - 1905 (2013/06/04)
A cationic Ir(I) complex-catalyzed O-to-N-alkyl migration in 2-alkoxypyridines bearing a secondary alkyl group on the oxygen atom by C-O bond cleavage is described. The present transformation gave various N-alkylpyridones in moderate to good yields. The addition of sodium acetate played a key role in suppressing β-hydrogen elimination.
