Synthesis of 3-azabicyclo[3.3.1]Nonane-6,9-diones

Brian D. Williams; Birute Williams; Francis Bernardoni; Robert C. Finn; Jon Zubieta

doi:10.3987/com-01-9319

Synthesis of 3-azabicyclo[3.3.1]Nonane-6,9-diones

Brian D. Williams, Birute Williams, Francis Bernardoni, Robert C. Finn, Jon Zubieta

Department of Chemistry

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

3 Scopus citations

Abstract

A one pot synthesis of 3-azabicyclo[3.3.1]nonane-6,9-diones is described via the additibn of acryloyl chloride to enamines of N-carboxy-4 piperidones. Yields of bicycle were highest when additions were made to vigorously boiling solutions of morpholine enamines. X-Ray analysis of an azabicyclic system revealed a chair-chair structure to be the preferred conformation. Hydrolysis of 3-azabicyclo[3.3.1]nonane-6,9-diones (IIa) and (IIb) yielded the monocyclic carboxylic acids (IIIa) and (IIIb).

Original language	English (US)
Pages (from-to)	2199-2206
Number of pages	8
Journal	Heterocycles
Volume	55
Issue number	11
DOIs	https://doi.org/10.3987/com-01-9319
State	Published - Nov 1 2001

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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title = "Synthesis of 3-azabicyclo[3.3.1]Nonane-6,9-diones",

abstract = "A one pot synthesis of 3-azabicyclo[3.3.1]nonane-6,9-diones is described via the additibn of acryloyl chloride to enamines of N-carboxy-4 piperidones. Yields of bicycle were highest when additions were made to vigorously boiling solutions of morpholine enamines. X-Ray analysis of an azabicyclic system revealed a chair-chair structure to be the preferred conformation. Hydrolysis of 3-azabicyclo[3.3.1]nonane-6,9-diones (IIa) and (IIb) yielded the monocyclic carboxylic acids (IIIa) and (IIIb).",

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T1 - Synthesis of 3-azabicyclo[3.3.1]Nonane-6,9-diones

AU - Williams, Brian D.

AU - Williams, Birute

AU - Bernardoni, Francis

AU - Finn, Robert C.

AU - Zubieta, Jon

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N2 - A one pot synthesis of 3-azabicyclo[3.3.1]nonane-6,9-diones is described via the additibn of acryloyl chloride to enamines of N-carboxy-4 piperidones. Yields of bicycle were highest when additions were made to vigorously boiling solutions of morpholine enamines. X-Ray analysis of an azabicyclic system revealed a chair-chair structure to be the preferred conformation. Hydrolysis of 3-azabicyclo[3.3.1]nonane-6,9-diones (IIa) and (IIb) yielded the monocyclic carboxylic acids (IIIa) and (IIIb).

AB - A one pot synthesis of 3-azabicyclo[3.3.1]nonane-6,9-diones is described via the additibn of acryloyl chloride to enamines of N-carboxy-4 piperidones. Yields of bicycle were highest when additions were made to vigorously boiling solutions of morpholine enamines. X-Ray analysis of an azabicyclic system revealed a chair-chair structure to be the preferred conformation. Hydrolysis of 3-azabicyclo[3.3.1]nonane-6,9-diones (IIa) and (IIb) yielded the monocyclic carboxylic acids (IIIa) and (IIIb).

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Synthesis of 3-azabicyclo[3.3.1]Nonane-6,9-diones

Abstract

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