19506-17-3Relevant articles and documents
POLYCYCLIC TLR7/8 ANTAGONISTS AND USE THEREOF IN THE TREATMENT OF IMMUNE DISORDERS
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, (2017/07/06)
The present invention relates to compounds of Formula (I) and pharmaceutically acceptable compositions thereof, useful as toll-like receptor 7/8 (TLR7/8) antagonists. In Formula (I), Ring A is aryl or heteroaryl; Ring B is aryl or heteroary; and X is C(R4)2, O, NR4, S, S(R4), or S(R4)2.
The Thermolysis of Polyazapentadienes. Part 2. Formation of Quinoxalines from 5-Aryl-1-phenyl-1,2,5-triazapentadienes
McNab, Hamish
, p. 1941 - 1946 (2007/10/02)
Thermolysis in the gas phase of 5-(p-substituted phenyl)-1-phenyl-1,2,5-triazapentadienes at 600 deg C and 10-2 Torr gives 6-substituted quinoxalines.The yield is ca. 30 percent, and is independent of the electronic nature of the substituent.The corresponding 5-(o-substituted) derivatives give 5-substituted quinoxalines, though the yield is lower, and quinoxaline itself is a major contaminant, due to ipso attack and ejection of the substituent. 5-(m-Substituted) derivatives give mixtures of 5- and 6-substituted quinoxalines on pyrolysis.The 5-isomer is dominant for compounds with m-alkyl substituents, while the 6-isomer is the major product for those with electron-withdrawing or electron-donating m-substituents.
Carbon-13 NMR Studies on some 5-Substituted Quinoxalines
Hollstein, Ulrich,Krisov, Galen E.
, p. 300 - 304 (2007/10/02)
Eleven 5-substituted quinoxalines (NO2, NH2, COOH, OCH3, CH3, OH, F, Cl, Br, I, CN, the latter five not reported previously) have been synthesized by standard methods.Their 13C NMR spectra have been measured in DMSO-d6 and assigned on the basis of substituent parameters, by line widths and by intensities.The chemical shifts compare favorably with those calculated using benzene substituent parameters, and are very close to those of corresponding carbons in 1-substituted phenazines.The correlation with the chemical shifts of the corresponding positions in 1-substituted naphthalenes is also close except for those of carbons 4a and 8a in the quinoxalines which, due to their proximity to nitrogen, are downfield (in some cases 12 ppm) of the signals of the corresponding carbons in naphthalene. 5-Fluoroquinoxaline was also measured in CDCl3, CD3COCD3, CD3CN, CD3OD, C6D6 and CD3COOD.In all solvents an abnormally low 2J(CF) (ca. 12 Hz) was found for C-4a and no C-F spin-spin splitting could be detected for the three-bond coupling of C-8a.Similar abnormalities were found in 2-fluoroaniline and 2-fluoroacetanilide.There are linear relationships between the Q parameter of the substituent and the chemical shift of carbons 4a, 5 and 6.A linear relationship also exists between the chemical shift of C-8 ('para' position) and the Hammett ?p parameter of the substituent.
