Use of Atom-transfer Radical Cyclizations as an Efficient Entry into a New Serotonergic Norazaadamantane

Daniel L. Flynn; Daniel Becker; Roger Nosal; Daniel Zabrowksi

doi:10.1016/S0040-4039(00)60166-1

Use of Atom-transfer Radical Cyclizations as an Efficient Entry into a New Serotonergic Norazaadamantane

Daniel L. Flynn, Daniel Becker, Roger Nosal, Daniel Zabrowksi

Department of Chemistry and Biochemistry

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

Abstract

A route to azanoradamantanes is described which makes use of an atom-transfer radical cyclization to afford 3-azabicyclo[3.3.0]octanes 3A and 3B. Subsequent elaboration of exo-allylamine functionality, followed by cyclization of the endo-hydroxymethyl intermediate 9, affords the new azanoradamantanes 11 and 4. This new azatricyclic system is useful for producing serotonin 5-HT3 antagonists and 5-HT4 agonists.

Original language	American English
Journal	Chemistry: Faculty Publications and Other Works
Volume	33
Issue number	48
DOIs	https://doi.org/10.1016/S0040-4039(00)60166-1
State	Published - Nov 24 1992

Keywords

atom-transfer radical cyclizations

Disciplines

Chemistry

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abstract = " A route to azanoradamantanes is described which makes use of an atom-transfer radical cyclization to afford 3-azabicyclo[3.3.0]octanes 3A and 3B. Subsequent elaboration of exo-allylamine functionality, followed by cyclization of the endo-hydroxymethyl intermediate 9, affords the new azanoradamantanes 11 and 4. This new azatricyclic system is useful for producing serotonin 5-HT3 antagonists and 5-HT4 agonists.",

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T1 - Use of Atom-transfer Radical Cyclizations as an Efficient Entry into a New Serotonergic Norazaadamantane

AU - Flynn, Daniel L.

AU - Becker, Daniel

AU - Nosal, Roger

AU - Zabrowksi, Daniel

PY - 1992/11/24

Y1 - 1992/11/24

N2 - A route to azanoradamantanes is described which makes use of an atom-transfer radical cyclization to afford 3-azabicyclo[3.3.0]octanes 3A and 3B. Subsequent elaboration of exo-allylamine functionality, followed by cyclization of the endo-hydroxymethyl intermediate 9, affords the new azanoradamantanes 11 and 4. This new azatricyclic system is useful for producing serotonin 5-HT3 antagonists and 5-HT4 agonists.

AB - A route to azanoradamantanes is described which makes use of an atom-transfer radical cyclization to afford 3-azabicyclo[3.3.0]octanes 3A and 3B. Subsequent elaboration of exo-allylamine functionality, followed by cyclization of the endo-hydroxymethyl intermediate 9, affords the new azanoradamantanes 11 and 4. This new azatricyclic system is useful for producing serotonin 5-HT3 antagonists and 5-HT4 agonists.

KW - atom-transfer radical cyclizations

UR - https://ecommons.luc.edu/chemistry_facpubs/7

U2 - 10.1016/S0040-4039(00)60166-1

DO - 10.1016/S0040-4039(00)60166-1

M3 - Article

VL - 33

JO - Chemistry: Faculty Publications and Other Works

JF - Chemistry: Faculty Publications and Other Works

IS - 48

ER -

Use of Atom-transfer Radical Cyclizations as an Efficient Entry into a New Serotonergic Norazaadamantane

Abstract

Keywords

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