Highly efficient synthesis of benzodioxins with a 2-site quaternary carbon structure by secondary amine-catalyzed dual Michael cascade reactionsElectronic supplementary information (ESI) available: Copies of the 1H, 13C and 19F NMR spectra of the products. See DOI: 10.1039/c8ob01029c

Salicylic acids and substituted ynones were employed as substrates to afford a class of valuable 4 H -benzo[ d ][1,3]dioxin-4-ones with a 2-site quaternary carbon structure in up to 92% yield by secondary amine-catalyzed dual Michael cascade reactions under mild reaction conditions. The α,β-unsatura...

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Main Authors He, Xuefeng, Li, Yongsu, Wang, Meng, Chen, Hui-Xuan, Chen, Bin, Liang, Hao, Zhang, Yaqi, Pang, Jiyan, Qiu, Liqin
Format Journal Article
LanguageEnglish
Published 01.08.2018
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Summary:Salicylic acids and substituted ynones were employed as substrates to afford a class of valuable 4 H -benzo[ d ][1,3]dioxin-4-ones with a 2-site quaternary carbon structure in up to 92% yield by secondary amine-catalyzed dual Michael cascade reactions under mild reaction conditions. The α,β-unsaturated ketone as the key intermediate in the cascade process was successfully separated and characterized. As a result, a new reaction route for ynone species is demonstrated, which is totally different from the existing allenamine activation model. Employing salicylic acids and substituted 3-butyn-2-ones as the substrates, a morpholine catalyzed tandem dual Michael addition afforded a benzodioxin skeleton.
Bibliography:Electronic supplementary information (ESI) available: Copies of the
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13
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10.1039/c8ob01029c
F NMR spectra of the products. See DOI
ISSN:1477-0520
1477-0539
DOI:10.1039/c8ob01029c