Sequential addition/annulation reactions of sulfinate and nitrite anions to b-(2-aminophenyl)-a,b-ynones led to valuable 4-sulfonylquinolines and 4-nitroquinolines. The latter proved to be versatile precursors of N-unsubstituted 4-aminoquinolines and 4-quinolones. Reaction of b-(2-aminophenyl)-a,b-ynones with DMF/NaOH resulted in the formation of 4-(dimethylamino)quinolines. The use of an alternative CO-free procedure for the preparation of substrates b-(2-aminophenyl)-a,b-ynones allowed extension of the methodology to the synthesis of 4-substituted 2-alkylquinolines.

An Improved Environmentally Friendly Approach to 4-Nitro-, 4-Sulfonyl-, and 4-Aminoquinolines and 4-Quinolones through Conjugate Addition of Nucleophiles to b-(2-Aminophenyl)-a,b-ynones

Rode, Navnath D.
Membro del Collaboration Group
;
Arcadi, Antonio
Membro del Collaboration Group
;
Chiarini, Marco
Membro del Collaboration Group
;
Marinelli, Fabio
Writing – Original Draft Preparation
2017-01-01

Abstract

Sequential addition/annulation reactions of sulfinate and nitrite anions to b-(2-aminophenyl)-a,b-ynones led to valuable 4-sulfonylquinolines and 4-nitroquinolines. The latter proved to be versatile precursors of N-unsubstituted 4-aminoquinolines and 4-quinolones. Reaction of b-(2-aminophenyl)-a,b-ynones with DMF/NaOH resulted in the formation of 4-(dimethylamino)quinolines. The use of an alternative CO-free procedure for the preparation of substrates b-(2-aminophenyl)-a,b-ynones allowed extension of the methodology to the synthesis of 4-substituted 2-alkylquinolines.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11697/118460
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