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Reaction Behaviour of Arylamines with Nitroalkenes in the Presence of Bismuth(III) Triflate: An Easy Access to 2,3-Dialkylquinolines

Abstract

We report the reaction behaviour between arylamines and nitroalkenes in the presence of bismuth(III) triflate (10 mol %) and diacetoxyiodobenzene (10 mol % ). We obtained 2,3-dialkylquinoline derivatives instead of expected 3-alkylindole derivatives. The present reaction is an alternate approach for the synthesis of 2,3-dialkylquinoline derivatives under milder conditions. Further, we estabilish the mechanistic pathway by theoretical calculation using Gaussian 09 software [B3LYP/6-311+G(d,p)] and it shows that the reaction prefers conventional aza-Michael reaction over Michael addition. Nitroalkenes behave in a different manner than aromatic nitoalkenes. Aza-Michael adduct gives rise to imine by the elimination of water which may tautomerize to correponding enamine. The resulted imine and enamine intermediates react together to afford the desired quinoline derivatives. This protocol provieded consecutive one C-N and two C-C bonds formation, high regioslectivity, broad substrate-scope and good yields.

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Article information


Submitted
12 Oct 2019
Accepted
11 Feb 2020
First published
12 Feb 2020

Org. Biomol. Chem., 2020, Accepted Manuscript
Article type
Paper

Reaction Behaviour of Arylamines with Nitroalkenes in the Presence of Bismuth(III) Triflate: An Easy Access to 2,3-Dialkylquinolines

S. Ali, R. Gattu, V. Singh, S. Mondal, A. T. Khan, G. Dubey and P. V. Bharatam, Org. Biomol. Chem., 2020, Accepted Manuscript , DOI: 10.1039/C9OB02214G

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