- TBAF-Catalyzed Tandem Synthesis of Triazolo[4,5-c]quinolines at Ambient Temperature
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A mild, efficient and metal-free synthetic method for 1H-[1,2,3]triazolo[4,5-c]quinolines has been developed via intermolecular [3+2] cycloaddition of β-(2-aminoaryl)-α,β-ynones and TMS-N3, followed by intramolecular dehydration annulation sequential reactions. With 5 mmol-% of TBAF as catalyst, the reaction can smoothly proceed in DMF at ambient temperature to afford a wide range of functionalized 1H-[1,2,3]triazolo[4,5-c]quinolines in good to excellent yields.
- Sun, Nan,Yang, Han,Zheng, Kai,Jin, Liqun,Hu, Baoxiang,Shen, Zhenlu,Hu, Xinquan
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supporting information
p. 6805 - 6812
(2020/11/02)
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- An Improved Environmentally Friendly Approach to 4-Nitro-, 4-Sulfonyl-, and 4-Aminoquinolines and 4-Quinolones through Conjugate Addition of Nucleophiles to β-(2-Aminophenyl)-α,β-ynones
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Sequential addition/annulation reactions of sulfinate and nitrite anions to β-(2-aminophenyl)-α,β-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 β-(2-aminophenyl)-α,β-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 β-(2-aminophenyl)-α,β-ynones allowed extension of the methodology to the synthesis of 4-substituted 2-alkylquinolines.
- Rode, Navnath D.,Arcadi, Antonio,Chiarini, Marco,Marinelli, Fabio
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p. 2501 - 2512
(2017/05/22)
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- The palladium-catalyzed transfer hydrogenation/heterocyclization of β- (2-aminophenyl)-α,β-ynones. An approach to 2-aryl- and 2-vinylquinolines
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The palladium-catalyzed transfer hydrogenation/cyclization of readily available β-(o-aminophenyl)-α,β-ynones I affords 2-aryl- and 2- vinylquinolines 3 in good yield.
- Cacchi, Sandro,Fabrizi, Giancarlo,Marinelli, Fabio
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p. 401 - 404
(2007/10/03)
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