Metalation/functionalization sequences applied to 2-bromo-3-fluoroquinolines

Mono- and disubstituted 2-bromo-3-fluoroquinolines are readily accessible. They can be converted into the 3-fluoroquinoline-2-carboxylic acids by consecutive halogen/metal permutation and into the 2-bromo-3-fluoroquinoline-4-carboxylic acids by consecutive deprotonation and carboxylation. The latter compds. can be reduced to afford the 3-fluoroquinoline-4-carboxylic acids. The yields are excellent throughout. Rather than introduction of one functional group alternatively at the 2- or 4-position, one may also attach two different functional groups sequentially to both sites. [on SciFinder (R)]


Published in:
Tetrahedron, 61, 3, 717-725
Year:
2005
Keywords:
Note:
CAN 142:176659
27-17
Heterocyclic Compounds (One Hetero Atom)
Institute of Chemical Sciences and Engineering, BCh,Ecole Polytechnique Federale,Lausanne,Switz.
Journal
0040-4020
written in English.
106-47-8 (4-Chloroaniline); 108-69-0 (3,5-Dimethylaniline); 615-36-1 (2-Bromoaniline); 124467-22-7; 175609-40-2; 175609-41-3; 834883-98-6 Role: RCT (Reactant), RACT (Reactant or reagent) (metalation/functionalization sequences applied to 2-bromo-3-fluoroquinolines); 834883-95-3P; 834883-96-4P; 834883-97-5P; 834883-99-7P; 834884-00-3P; 834884-01-4P; 834884-03-6P; 834884-04-7P; 834884-05-8P; 834884-13-8P; 834884-14-9P; 834884-15-0P; 834884-16-1P; 834884-17-2P; 834884-18-3P; 834884-25-2P; 834884-26-3P; 834884-27-4P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (metalation/functionalization sequences applied to 2-bromo-3-fluoroquinolines); 396-31-6P (3-Fluoroquinoline); 153880-32-1P (3-Fluoroquinoline-4-carboxylic acid); 834884-06-9P; 834884-07-0P; 834884-08-1P; 834884-09-2P; 834884-10-5P; 834884-11-6P; 834884-12-7P; 834884-19-4P; 834884-20-7P; 834884-21-8P; 834884-22-9P; 834884-23-0P; 834884-24-1P; 834884-28-5P Role: SPN (Synthetic preparation), PREP (Preparation) (metalation/functionalization sequences applied to 2-bromo-3-fluoroquinolines)
Laboratories:




 Record created 2006-03-03, last modified 2018-01-27


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