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Short Paper | Regular issue | Vol 104, No. 2, 2022, pp.365-378
Published online, 15th November, 2021
DOI: 10.3987/COM-21-14570
Synthesis and NMR Spectroscopic Characteristics of Novel Polysubstituted Quinolines Incorporating Furoxan Moiety

Trinh Thi Huan, Le Thi Hoa, and Nguyen Huu Dinh*

*Department of Chemistry, Hanoi National University of Education, 136 Xuan Thuy, Hanoi, Vietnam

Abstract

5,6-Dimethoxy-8-(3-methylfuroxan-4-yl)-2-methylquinoline (1) and 5,6-dimethoxy-8-(3-methylfuroxan-4-yl)quinoline-2-carbaldehyde (2) were synthesized. The condensation of 1 with some nitrobenzaldehydes catalyzed by acetic acid under mild conditions gave four styrylquinolines (1a-d). The condensation of 2 with methyl phenyl ketones catalyzed by potassium hydroxide at room temperature afforded six polysubstituted α,β-unsaturated ketones (2a-f). All proton and carbon signals of obtained compounds were assigned based on analyzing the spin–spin splitting patterns and on the cross peaks in their HSQC and HMBC spectra. ROESY spectrum analysis showed that for (E)-3-(quinolin-2-yl)-1-phenylprop-2-en-1-ones Hα resonated in a weaker field as compared to Hβ.