100366-75-4Relevant articles and documents
Fine-tuning the oxidative ability of persistent radicals: Electrochemical and computational studies of substituted 2-pyridylhydroxylamines
Bogart, Justin A.,Lee, Heui Beom,Boreen, Michael A.,Jun, Minsik,Schelter, Eric J.
, p. 6344 - 6349 (2013)
N-tert-Butyl-N-2-pyridylhydroxylamines were synthesized from 2-halopyridines and 2-methyl-2-nitrosopropane using magnesium-halogen exchange. The use of Turbo Grignard generated the metallo-2-pyridyl intermediate more reliably than alkyllithium reagents. The hydroxylamines were characterized using NMR, electrochemistry, and density functional theory. Substitution of the pyridyl ring in the 3-, 4-, and 5-positions was used to vary the potential of the nitroxyl/oxoammonium redox couple by 0.95 V. DFT computations of the electrochemical properties agree with experiment and provide a toolset for the predictive design of pyridyl nitroxides.
Recommendable routes to trifluoromethyl-substituted pyridine- and quinolinecarboxylic acids
Cottet, Fabrice,Marull, Marc,Lefebvre, Olivier,Schlosser, Manfred
, p. 1559 - 1568 (2007/10/03)
As part of a case study, rational strategies for the preparation of all ten 2-, 3-, or 4-pyridinecarboxylic acids and all nine 2-, 3-, 4-, or 8-quinolinecarboxylic acids bearing trifluoromethyl substituents at the 2-, 3-, or 4-position were elaborated. The trifluoromethyl group, if not already present in the precursor, was introduced either by the deoxygenative fluorination of suitable carboxylic acids with sulfur tetrafluoride or by the displacement of ring-bound bromine or iodine by trifluoromethylcopper generated in situ. The carboxy function was produced by treatment of organolithium or organomagnesium intermediates, products of halogen/metal or hydrogen/ metal permutation, with carbon dioxide. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).
Synthesis of thieno[2,3-b]quinoxalines from 2-haloquinoxalines
Armengol, Montserrat,Joule, John A.
, p. 154 - 158 (2007/10/03)
Thieno[2,3-b]quinoxalines were synthesized from 2-haloquinoxalines using palladium catalyst. The coupling of latter with alkynes and addition of one mol equivalent of bromine to the 2-alkynylquinoxalines thus produced was described. The resulting dibromid