Inter- and Intramolecular [4+2]-Cycloaddition Reactions with 4,4-Disubstituted N-Silyl-1,4-dihydropyridines as Precursors for N-Protonated 2-Azabutadiene Intermediates

Cornelia E. Schmaunz; Peter Mayer; Klaus T. Wanner

doi:10.1055/s-0033-1341044

Synthesis, Table of Contents

Synthesis 2014; 46(12): 1630-1638
DOI: 10.1055/s-0033-1341044

paper

Inter- and Intramolecular [4+2]-Cycloaddition Reactions with 4,4-Disubstituted N-Silyl-1,4-dihydropyridines as Precursors for N-Protonated 2-Azabutadiene Intermediates

Cornelia E. Schmaunz

^aDepartment of Pharmacy – Center for Drug Research, Ludwig-Maximilians-Universität München, Butenandtstr. 5-13, Haus C, 81377 München, Germany Fax: +49(89)218077247 Email: klaus.wanner@cup.uni-muenchen.de

,

Peter Mayer

^bDepartment of Chemistry, Ludwig-Maximilians-Universität München, Butenandtstr. 5-13, Haus D, 81377 München, Germany

,

Klaus T. Wanner*

^aDepartment of Pharmacy – Center for Drug Research, Ludwig-Maximilians-Universität München, Butenandtstr. 5-13, Haus C, 81377 München, Germany Fax: +49(89)218077247 Email: klaus.wanner@cup.uni-muenchen.de

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Abstract

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Abstract

An efficient and straightforward method for the synthesis of polycyclic ring systems with a central 2-azabicyclo[2.2.2]octane unit is developed. The process is based on [4+2]-cycloaddition reactions that are performed with N-protonated 2-azabutadiene intermediates as heterodienes, generated from 4,4-disubstituted N-silyl 1,4-dihydropyridines. As dienophiles, cyclopentadiene for the intermolecular cycloaddition and an allyl moiety already attached to the 4,4-disubstituted 1,4-dihydropyridines for the intramolecular variant, are used.

Key words

hetero-Diels–Alder reaction - 1,4-dihydropyridines - heterocycles - polycycles - imines

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References

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