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Journal article

2-(Trifluoromethyl)quinolines from anilines: a novel mode of isomerization and cyclization

Deprotonation of N-ethylidene-tert-butylamine with lithium diisopropylamide and subsequent condensation with Et trifluoroacetate gives 4-tert-butylamino-1,1,1-trifluorobut-3-en-2-one. An exchange of the amino substituent occurs when the latter compd. is treated with anilines under mildly acidic conditions. When heated in the presence of phosphoryl trichloride, the resulting 4-anilino-1,1,1-trifluorobut-3-en-2-ones undergo an N -> ortho shift of the side chain followed by cyclization and dehydration to afford 2-(trifluoromethyl)quinolines. [on SciFinder (R)]

    Keywords: Isomerization; Ring closure and formation (prepn. of (trifluoromethyl)quinolines from anilines and tert-butylaminotrifluorobutenones) ; quinoline trifluoromethyl prepn; cyclization isomerization aniline aminobutenone

    Note:

    CAN 124:343078

    27-17

    Heterocyclic Compounds (One Hetero Atom)

    Inst. Chimie Organique de l'Universite,Batiment de Chimie,Lausanne-Dorigny,Switz.

    Journal

    0040-4020

    written in English.

    324-33-4P; 347-42-2P; 1860-46-4P; 1860-47-5P; 176722-63-7P; 176722-64-8P; 176722-65-9P; 176722-66-0P; 176722-67-1P; 176722-68-2P; 176722-69-3P; 176722-70-6P; 176722-71-7P; 176722-72-8P; 176722-73-9P; 176722-74-0P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 62-53-3 (Aniline); 95-53-4 (o-Toluidine); 106-40-1 (4-Bromoaniline); 106-49-0 (p-Toluidine); 108-42-9 (3-Chloroaniline); 108-44-1; 372-19-0 (3-Fluoroaniline); 372-39-4 (3,5-Difluoroaniline); 383-63-1 (Ethyl trifluoroacetate); 536-90-3; 591-19-5 (3-Bromoaniline); 615-36-1 (2-Bromoaniline); 7020-80-6 (N-Ethylidene-tert-butylamine); 10272-07-8 (3,5-Dimethoxyaniline) Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of (trifluoromethyl)quinolines from anilines and tert-butylaminotrifluorobutenones); 176722-50-2P; 176722-51-3P; 176722-52-4P; 176722-53-5P; 176722-54-6P; 176722-55-7P; 176722-56-8P; 176722-57-9P; 176722-58-0P; 176722-59-1P; 176722-60-4P; 176722-61-5P; 176722-62-6P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of (trifluoromethyl)quinolines from anilines and tert-butylaminotrifluorobutenones)

    Reference

    Record created on 2006-03-03, modified on 2016-08-08

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