Trifluoromethylated (tetrahydropyrrolo) quinazolinones by a new three-component reaction and facile assignment of the regio- and stereoisomers formed by NMR spectroscopy

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 cycl...

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Bibliographic Details
Published in:Magnetic resonance in chemistry 2010-05, Vol.48 (5), p.375-385
Main Authors: Dolenský, Bohumil, Kvíčala, Jaroslav, Paleta, Oldřich, Lang, Jan, Dvořáková, Hana, Čejka, Jan
Format: Article
Language:English
Subjects:
1-b]quinazolinone
19F NMR
3-trifluoropyruvate
Adaptation
Diffraction
Fluorine - chemistry
heteronuclear DPFGSE-NOE
Magnetic resonance
Magnetic Resonance Spectroscopy - methods
methyl 3
methyl 3,3,3‐trifluoropyruvate
NMR
NMR spectroscopy
Quinazolinones
Quinazolinones - chemistry
relative configuration
Stereoisomerism
stereoisomers
tetrahydropyrrolo
tetrahydropyrrolo[2,1‐b]quinazolinone
three-component cyclisation
trifluoromethylated heterocycles
X-rays
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Summary: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. Copyright © 2010 John Wiley & Sons, Ltd. 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.
ISSN:0749-1581
1097-458X
1097-458X
DOI:10.1002/mrc.2580