Highly efficient synthesis of benzodioxins with a 2-site quaternary carbon structure by secondary amine-catalyzed dual Michael cascade reactions

Organic & Biomolecular Chemistry
Xuefeng HeLiqin Qiu

Abstract

Salicylic acids and substituted ynones were employed as substrates to afford a class of valuable 4H-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.

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Citations

Oct 30, 2020·Organic & Biomolecular Chemistry·Zhen-Zhen XieHua Yang
Feb 5, 2021·Organic & Biomolecular Chemistry·Sengodagounder MuthusamyEringathodi Suresh

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Methods Mentioned

BETA
NMR

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