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

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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Published inOrganic & biomolecular chemistry Vol. 16; no. 30; pp. 5533 - 5538
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 CAMBRIDGE Royal Soc Chemistry 2018
Royal Society of Chemistry
Subjects
Carbon
Cascade chemical reactions
Chemical reactions
Chemistry
Chemistry, Organic
Dioxins
Physical Sciences
Science & Technology
Substrates
ALCOHOLS
SALICYLIHALAMIDE
NUCLEOPHILES
KETONES
ACID
ACYL TRANSFER-CYCLIZATION
INHIBITORS
FACILE
SALICYLATES
DERIVATIVES
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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.
Bibliography:ObjectType-Article-1
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ISSN:1477-0520
1477-0539
1477-0539
DOI:10.1039/C8OB01029C