Intramolecular electrophilic aromatic substitution reactions of 2-amidoacroleins: A new method for the preparation of tetrahydroisoquinolines, tetrahydro-3-benzazepines, and hexahydro-3-benzazocines

James R. Fuchs; Raymond L. Funk

doi:10.1021/ol016592n

Intramolecular electrophilic aromatic substitution reactions of 2-amidoacroleins: A new method for the preparation of tetrahydroisoquinolines, tetrahydro-3-benzazepines, and hexahydro-3-benzazocines

James R. Fuchs, Raymond L. Funk

Chemistry

Research output: Contribution to journal › Article › peer-review

41 Scopus citations

Abstract

Equation presented A variety of heterocyclic ring systems can be prepared by subjecting N-aryl-substituted 5-amido-1,3-dioxins to Lewis acids. The reactions proceed via catalyzed retrocycloadditions to afford 2-amidoacroleins and concomitant regioselective electrophilic aromatic substitution reactions. The transformation is also successful using dioxins with amides that are within the incipient ring to afford the analogous lactams.

Original language	English (US)
Pages (from-to)	3349-3351
Number of pages	3
Journal	Organic Letters
Volume	3
Issue number	21
DOIs	https://doi.org/10.1021/ol016592n
State	Published - Oct 18 2001

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol016592n

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abstract = "Equation presented A variety of heterocyclic ring systems can be prepared by subjecting N-aryl-substituted 5-amido-1,3-dioxins to Lewis acids. The reactions proceed via catalyzed retrocycloadditions to afford 2-amidoacroleins and concomitant regioselective electrophilic aromatic substitution reactions. The transformation is also successful using dioxins with amides that are within the incipient ring to afford the analogous lactams.",

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AU - Fuchs, James R.

AU - Funk, Raymond L.

PY - 2001/10/18

Y1 - 2001/10/18

N2 - Equation presented A variety of heterocyclic ring systems can be prepared by subjecting N-aryl-substituted 5-amido-1,3-dioxins to Lewis acids. The reactions proceed via catalyzed retrocycloadditions to afford 2-amidoacroleins and concomitant regioselective electrophilic aromatic substitution reactions. The transformation is also successful using dioxins with amides that are within the incipient ring to afford the analogous lactams.

AB - Equation presented A variety of heterocyclic ring systems can be prepared by subjecting N-aryl-substituted 5-amido-1,3-dioxins to Lewis acids. The reactions proceed via catalyzed retrocycloadditions to afford 2-amidoacroleins and concomitant regioselective electrophilic aromatic substitution reactions. The transformation is also successful using dioxins with amides that are within the incipient ring to afford the analogous lactams.

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U2 - 10.1021/ol016592n

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Intramolecular electrophilic aromatic substitution reactions of 2-amidoacroleins: A new method for the preparation of tetrahydroisoquinolines, tetrahydro-3-benzazepines, and hexahydro-3-benzazocines

Abstract

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