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

A one pot synthesis of 3-azabicyclo[3.3.1]nonane-6,9-diones is described via the addition of acryloyl chloride to enamines of N-carboxy-4piperidones. Yields of bicycle were highest when additions were made to vigorously boiling solutions of morpholine enamines. X-Ray analysis of an azabicyclic syste...

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Bibliographic Details
Published inHeterocycles Vol. 55; no. 11; pp. 2199 - 2206
Main Authors Williams, BD, Williams, B, Bernardoni, F, Finn, RC, Zubieta, J
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 01.11.2001
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
unsaturated acid chloride
BICYCLO<3.3.1>NONANES
NMR-SPECTROSCOPY
STEREOCHEMISTRY
ENAMINES
piperidone
cyclization
enamine
CONFORMATIONS
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Summary:A one pot synthesis of 3-azabicyclo[3.3.1]nonane-6,9-diones is described via the addition of acryloyl chloride to enamines of N-carboxy-4piperidones. 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).
ISSN:0385-5414
1881-0942
DOI:10.3987/com-01-9319