Accessing Tricyclic Imines Comprising a 2-Azabicyclo[2.2.2]octane Scaffold by Intramolecular Hetero-Diels-Alder Reaction of 4-Alkenyl-Substituted N-Silyl-1,4-dihydropyridines

Tricyclic imines inheriting a 2-azabicyclo[2.2.2]octane (isoquinuclidine) scaffold were provided with high regioselectivity in moderate to very good yields by a smooth, broadly applicable intramolecular hetero-Diels-Alder reaction of various 4-omega-alkenyl-substituted 1,4-dihydropyridines (DHPs) un...

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Bibliographic Details
Published inSynthesis (Stuttgart) Vol. 51; no. 22; pp. 4296 - 4310
Main Authors Rudy, Heinrich-Karl A., Wanner, Klaus T.
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.11.2019
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
intramolecular hetero-Diels-Alder reaction
REAGENTS
CONVENIENT METHOD
PYRIDINE
ALKYLATION
diorganomagnesium reagents
4-ARYL-1,4-DIHYDROPYRIDINES
SALTS
2-azabicy-clo[2,2,2]octane
heterocycles
CHEMISTRY
1,4-dihydropyridines
REGIOSELECTIVE ADDITION
polycycles
ION-MEDIATED CYCLIZATIONS
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Summary:Tricyclic imines inheriting a 2-azabicyclo[2.2.2]octane (isoquinuclidine) scaffold were provided with high regioselectivity in moderate to very good yields by a smooth, broadly applicable intramolecular hetero-Diels-Alder reaction of various 4-omega-alkenyl-substituted 1,4-dihydropyridines (DHPs) under trifluoroacetic acid catalysis. The required- 4,4-disubstituted 1,4-DHPs were obtained by introduction of omega-alkenyl moieties of varying chain length via diorganomagnesium reagents into the 4-position of diversely 4-substituted pyridines after prior N-activation with triisopropylsilyltriflate.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0039-1690619