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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.popowyczinsa-lyon.fr, paolo.lariniuniv-lyon1.fr

H. Lavrard, P. Larini, F. Popowycz, Org. Lett., 2017, 19, 4203-4206.

DOI: 10.1021/acs.orglett.7b01798 (free Supporting Information)


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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

quinolines


ID: J54-Y2017