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Journal
2008 | 6 | 2 | 161-174
Article title

Azabrendanes V. Synthesis and reactions of stereoisomeric exo- and endo-5-aminomethylbicyclo[2.2.1]hept-2-ene-based ureas

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Abstracts
EN
A number of stereoisomeric ureas (N-[aryl(benzyl, or cycloalkyl)carbamoyl]-exo(endo)-5-aminomethylbicyclo[2.2.1]hept-2-enes) have been synthesized from bicyclo[2.2.1]hept-2-en-exo(endo)-5-carbonitrile by reduction with lithium aluminum hydride and subsequent reaction of the resulting amines with aryl (benzyl, or cycloalkyl) isocyanates. Regioselective alkylation of stereoisomeric ureas has been performed with benzyl chloride under liquid/solid phase-transfer catalysis. The outcome of the reactions of ureas with peroxy acids is dependent upon the orientation of substituents in the bicyclic fragment. Exo-isomeric ureas are transformed into corresponding epoxy-derivatives, while reactions of the endo-isomers are accompanied by intramolecular cyclization, resulting in the formation of azatricyclononane derivatives. Quantum-chemical calculations have established a decisive role for additional hydrogen bonding in the stabilization of transition states in these heterocyclization reactions of ureas. The structures and stereochemical homogeneity of the products have been confirmed by the analysis of 1H and 13C NMR spectra and correlation spectroscopy. The mechanism of the intramolecular heterocyclization reaction of ureas and carboxamide of endo-5-aminomethyl-exo-2,3-epoxybicyclo[2.2.1]heptane series has been studied at the BHandHLYP/6-31G(d) level of theory. [...]
Publisher

Journal
Year
Volume
6
Issue
2
Pages
161-174
Physical description
Dates
published
1 - 6 - 2008
online
17 - 4 - 2008
Contributors
author
  • Department of Chemistry, Dnepropetrovsk National University, Dnepropetrovsk, 49625, Ukraine
author
  • ProBioGen A.G., D-13086, Berlin, Germany
author
  • Department of Chemistry, Dnepropetrovsk National University, Dnepropetrovsk, 49625, Ukraine
  • Department of Chemistry, Dnepropetrovsk National University, Dnepropetrovsk, 49625, Ukraine, sokovyty@ccmsi.us
  • Department of Chemistry, Dnepropetrovsk National University, Dnepropetrovsk, 49625, Ukraine
author
  • Department of Chemistry, Dnepropetrovsk National University, Dnepropetrovsk, 49625, Ukraine
  • Department of Chemistry, Jackson State University, Jackson, MS, 39217-0510, USA
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Document Type
Publication order reference
Identifiers
YADDA identifier
bwmeta1.element.-psjd-doi-10_2478_s11532-008-0012-9
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