Superacidic Cyclization of Activated Anthranilonitriles into 2-Unsubstituted-4-aminoquinolines
Hubert Lavrard, Paolo Larini* and Florence Popowycz*
*Université Lyon 1, Avenue Albert Einstein, F-69621
Villeurbanne Cedex; Université Lyon 1, 43 Bd du 11 novembre 1918, F-69622
Villeurbanne, France, Email: florence.popowycz
insa-lyon.fr,
paolo.lariniuniv-lyon1.fr
H. Lavrard, P. Larini, F. Popowycz, Org. Lett., 2017, 19, 4203-4206.
DOI: 10.1021/acs.orglett.7b01798
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Abstract
4-Aminoquinolines can be prepared in a three-step synthesis: A condensation of substituted anthranilonitriles with 1,1,1-trichloro-4-ethoxybut-3-enone proceeded efficiently either neat or in refluxing EtOH. Cyclization in superacidic trifluoromethanesulfonic acid provided an unstable intermediate, which upon treatment with NaOEt in ethanol, afforded the expected ethyl 4-aminoquinoline-3-carboxylates.
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Key Words
ID: J54-Y2017
