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Czasopismo
2008 | 6 | 2 | 161-174
Tytuł artykułu

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

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Warianty tytułu
Języki publikacji
EN
Abstrakty
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. [...]
Wydawca

Czasopismo
Rocznik
Tom
6
Numer
2
Strony
161-174
Opis fizyczny
Daty
wydano
2008-06-01
online
2008-04-17
Twórcy
  • Department of Chemistry, Dnepropetrovsk National University, Dnepropetrovsk, 49625, Ukraine
  • ProBioGen A.G., D-13086, Berlin, Germany
  • 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
autor
  • Department of Chemistry, Dnepropetrovsk National University, Dnepropetrovsk, 49625, Ukraine
  • Department of Chemistry, Jackson State University, Jackson, MS, 39217-0510, USA
Bibliografia
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Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.-psjd-doi-10_2478_s11532-008-0012-9
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