Superelectrophilic nazarov cyclizations with N-heterocycles

A series of Nazarov cyclizations has been studied involving N-heterocyclic-substituted 1-arylprop-2-en-1-one derivatives (aza-chalcones). Superacid catalyzed reactions of these derivatives provide good yields of heterocyclic-substituted 1-indanones. A mechanism is proposed involving diprotonated, su...

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Bibliographic Details
Published inTetrahedron Vol. 76; no. 47; pp. 131644 - 131650
Main Authors Vuong, Hien, Amadou, Harouna, Stentzel, Michael R., Klumpp, Douglas A.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 20.11.2020
Elsevier
Subjects
Chemistry
Chemistry, Organic
Heterocycles
Indanone
Nazarov
Physical Sciences
Science & Technology
Superacid
Superelectrophile
Indanone
Superacid
Heterocycles
Superelectrophile
Nazarov
ACTIVATION
ACID
ONE-POT SYNTHESIS
CATALYZED REACTIONS
BEHAVIOR
ARYLVINYLKETONES
1-INDANONES
1-PHENYL-2-PROPEN-1-ONES
INDANONES
DERIVATIVES
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Summary:A series of Nazarov cyclizations has been studied involving N-heterocyclic-substituted 1-arylprop-2-en-1-one derivatives (aza-chalcones). Superacid catalyzed reactions of these derivatives provide good yields of heterocyclic-substituted 1-indanones. A mechanism is proposed involving diprotonated, superelectrophilic intermediates. [Display omitted] •This chemistry provides easy access to heterocyclic-substituted indanones.•A mechanism is proposed involving dicationic intermediates.•The chemistry works best in excess superacid.
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2020.131644