3-Fluoro-2-quinolones From Anilines
N-(Fluoro-3-methoxyacryloyl)anilines [2-fluoro-3-methoxy-2-propenanilides] can be prepd. by condensation between lithium anilides and Me 2-fluoro-3-methoxy-2-propenoate. For example, the reaction of (E)- and (Z)-2-fluoro-3-methoxy-2-propenoic acid Me ester with aniline gave (E)- and (Z)-2-fluoro-3-methoxy-N-phenyl-2-propenoic acid Me ester. The cyclocondensation of the latter gave 3-fluoro-2(1H)-quinolinone. Under strongly acidic conditions, these intermediate undergo a cyclization reaction accompanied by elimination of methanol to give 3-fluoro-2-quinolones. Substituents occupying the para or ortho position of the aniline appear at the heterocyclic 6- and 8-positions, resp. In general, substituents attached to the meta position of the aniline lead to 1:1 mixts. of regioisomers. Only m-anisidine [3-methoxy-aniline] and m-fluoroaniline made an exception: they gave mainly the 7- and only trace amts. of the 5-substituted quinolone. [on SciFinder (R)]
1996
52
9
3223
8
CAN 124:289216
27-17
Heterocyclic Compounds (One Hetero Atom)
Inst. Chim. Org. l'Universite,Batiment Chim. (BCh),Lausanne-Dorigny,Switz.
Journal
written in English.
90-41-5 (2-Phenylaniline) Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. . of fluoroquinolinones by cyclocondensation of N-phenylpropenamides); 95-53-4 (2-Methylaniline); 98-16-8 (3-(Trifluoromethyl)aniline); 99-09-2 (3-Nitroaniline); 104-94-9 (4-Methoxyaniline); 108-42-9 (3-Chloroaniline); 108-44-1 (3-Methylaniline); 348-54-9 (2-Fluoroaniline); 371-40-4 (4-Fluoroaniline); 372-19-0 (3-Fluoroaniline); 455-14-1 (4-(Trifluoromethyl)aniline); 536-90-3 (3-Methoxyaniline) Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of fluoroquinolinones by cyclocondensation of N-phenylpropenamides); 175609-42-4P; 175609-43-5P; 175609-44-6P; 175609-45-7P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of fluoroquinolinones by cyclocondensation of N-phenylpropenamides); 124467-22-7P (3-Fluoro-2(1H)-quinolinone); 175609-36-6P; 175609-37-7P; 175609-38-8P; 175609-39-9P; 175609-40-2P; 175609-41-3P; 175609-63-9P; 175609-64-0P; 175609-65-1P; 175609-66-2P; 175609-67-3P; 175609-68-4P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of fluoroquinolinones by cyclocondensation of N-phenylpropenamides); 62-53-3 (Aniline); 175609-69-5; 175609-70-8 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of fluoroquinolinones from (alkoxy)-N-phenylpropenamides); 175609-27-5P; 175609-28-6P; 175609-29-7P; 175609-33-3P; 175609-46-8P; 175609-47-9P; 175609-48-0P; 175609-49-1P; 175609-50-4P; 175609-51-5P; 175609-52-6P; 175609-53-7P; 175609-54-8P; 175609-55-9P; 175609-56-0P; 175609-57-1P; 175609-59-3P; 175609-60-6P; 175609-61-7P; 175609-62-8P; 175609-71-9P; 175609-72-0P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of fluoroquinolinones from (alkoxy)-N-phenylpropenamides); 175609-30-0P; 175609-31-1P; 175609-32-2P; 175609-34-4P; 175609-35-5P; 175609-58-2P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of fluoroquinolinones from (alkoxy)-N-phenylpropenamides)
REVIEWED
EPFL