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

Authors
Williams, BD Williams, B Bernardoni, F Finn, RC Zubieta, J
Citation
Bd. Williams et al., Synthesis of 3-azabicyclo[3.3.1]nonane-6,9-diones, HETEROCYCLE, 55(11), 2001, pp. 2199-2206
Citations number
29
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
55
Issue
11
Year of publication
2001
Pages
2199 - 2206
Database
ISI
SICI code
0385-5414(20011101)55:11<2199:SO3>2.0.ZU;2-T
Abstract
A one pot synthesis of 3-azabicyclo[3.3.1]nonane-6,9-diones is described vi a the addition of acryloyl chloride to enamines of N-carboxy-4piperidones. Yields of bicycle were highest when additions were made to vigorously boili ng solutions of morpholine enamines. X-Ray analysis of an azabicyclic syste m revealed a chair-chair structure to be the preferred conformation. Hydrol ysis of 3-azabicyclo[3.3.1]nonane-6,9-diones (IIa) and (IIb) yielded the mo nocyclic carboxylic acids (IIIa) and (IIIb).