Recommendable routes to trifluoromethyl-substituted pyridine- and quinolinecarboxylic acids

As part of a case study, rational strategies for the prepn. 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. [on SciFinder (R)]


Published in:
European Journal of Organic Chemistry, 8, 1559-1568
Year:
2003
Keywords:
Note:
CAN 139:214305 27-17 Heterocyclic Compounds (One Hetero Atom) Institut de Chimie moleculaire et Biologique,Ecole Polytechnique Federale,Lausanne,Switz. Journal 1434-193X written in English. 102-92-1 (Cinnamoyl chloride); 368-48-9 (2-Trifluoromethylpyridine); 615-36-1 (2-Bromoaniline); 624-28-2 (2,5-Dibromopyridine); 18706-25-7; 52334-81-3; 65753-47-1; 77332-76-4; 81290-20-2 ((Trifluoromethyl)trimethylsilane); 81565-18-6; 128676-85-7 (2-Chloro-3-iodoquinoline); 189278-27-1; 587885-93-6; 587886-11-1; 590371-90-7; 590372-06-8; 590372-17-1; 590372-20-6 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of trifluoromethyl-substituted pyridine- and quinolinecarboxylic acids); 13534-89-9P (2,3-Dibromopyridine); 25199-86-4P; 30766-11-1P; 50488-42-1P; 52200-48-3P; 67805-67-8P; 71910-51-5P; 100366-75-4P; 163485-86-7P; 175205-81-9P; 175205-82-0P; 176722-63-7P; 223463-13-6P (5-Bromo-2-iodopyridine); 408502-43-2P; 436799-32-5P; 505084-55-9P; 505084-56-0P; 505084-58-2P; 505084-59-3P; 590371-58-7P; 590371-71-4P; 590371-73-6P; 590371-81-6P; 590371-88-3P; 590371-93-0P; 590371-95-2P; 590371-97-4P; 590372-03-5P; 590372-08-0P; 590372-14-8P; 590372-23-9P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of trifluoromethyl-substituted pyridine- and quinolinecarboxylic acids); 18706-39-3P; 80194-69-0P; 87407-12-3P; 131747-40-5P; 131747-41-6P; 131747-42-7P; 131747-43-8P; 155495-82-2P; 158063-66-2P; 231291-22-8P; 587886-26-8P; 588702-62-9P; 588702-63-0P; 588702-64-1P; 588702-65-2P; 588702-66-3P; 588702-67-4P; 590371-38-3P; 590371-53-2P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of trifluoromethyl-substituted pyridine- and quinolinecarboxylic acids)
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 Record created 2006-03-03, last modified 2018-01-27


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