Document Detail

Trifluoromethylated (tetrahydropyrrolo) quinazolinones by a new three-component reaction and facile assignment of the regio- and stereoisomers formed by NMR spectroscopy.
MedLine Citation:
PMID:  20301203     Owner:  NLM     Status:  MEDLINE    
A new three-component cyclisation reactions of methyl 3,3,3-trifluoropyruvate, 2-aminobenzylamine and oxo compounds afforded tetrahydropyrroloquinazolinones of the types 4 and 5 as mixtures of regio- and stereoisomers. Whereas standard 1D NMR spectroscopy was used for a facile assignment of the cyclization regioisomers, a combination of homo (proton-proton) and heteronuclear (proton-fluorine) NOE experiments allowed the determination of the relative configuration on stereogenic centres. The structure of some compounds was also confirmed by the X-ray diffraction. Adaptation of the 1D double-pulsed field-gradient spin-echo NOE for a heteronuclear case is presented.
Bohumil Dolenský; Jaroslav Kvícala; Oldrich Paleta; Jan Lang; Hana Dvoráková; Jan Cejka
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Magnetic resonance in chemistry : MRC     Volume:  48     ISSN:  1097-458X     ISO Abbreviation:  Magn Reson Chem     Publication Date:  2010 May 
Date Detail:
Created Date:  2010-04-14     Completed Date:  2010-07-12     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9882600     Medline TA:  Magn Reson Chem     Country:  England    
Other Details:
Languages:  eng     Pagination:  375-85     Citation Subset:  IM    
Copyright Information:
Copyright 2010 John Wiley & Sons, Ltd.
Department of Analytical Chemistry, Faculty of Chemical Engineering, Prague Institute of Chemical Technology, Technická 5, 16628 Prague 6, Czech Republic.
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MeSH Terms
Fluorine / chemistry
Magnetic Resonance Spectroscopy / methods*
Quinazolinones / chemistry*
Reg. No./Substance:
0/Quinazolinones; 7782-41-4/Fluorine

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