Multicomponent Cascade Reaction of 3‑Formylchromones: Highly Selective Synthesis of Functionalized 9‑Azabicyclo[3.3.1]nonane Derivatives

A novel protocol for the preparation of functionalized 9-azabicyclo[3.3.1]­nonane (ABCN) derivatives from 3-formylchromones, enaminones, and heterocyclic ketene aminals (HKAs) through an unprecedented cascade reaction has been developed by simply refluxing the mixture of the substrates 1–3. As a res...

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Bibliographic Details
Published inOrganic letters Vol. 23; no. 17; pp. 6866 - 6871
Main Authors Duan, Ying-Gang, Hu, Xing-Mei, Cao, Xin-Ling, Lv, Kai-Hong, Yan, Sheng-Jiao
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 03.09.2021
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CHROMONE
1,1-ENEDIAMINES SYNTHESIS
ISATINS
SITES
RECEPTOR
COCAINE
ENAMINES
CYCLIZATION
DISCOVERY
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Summary:A novel protocol for the preparation of functionalized 9-azabicyclo[3.3.1]­nonane (ABCN) derivatives from 3-formylchromones, enaminones, and heterocyclic ketene aminals (HKAs) through an unprecedented cascade reaction has been developed by simply refluxing the mixture of the substrates 1–3. As a result, a series of ABCNs were produced through a very complex cascade reaction. This protocol can be used in the synthesis of ABCNs that are suitable for combinatorial and parallel syntheses of ABCN natural-like products in a one-pot reaction.
Bibliography:ObjectType-Article-1
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c02431