Trifluoromethylated (tetrahydropyrrolo) quinazolinones by a new three-component reaction and facile assignment of the regio- and stereoisomers formed by NMR spectroscopy.
Bohumil Dolenský, Jaroslav Kvícala, Oldrich Paleta, Jan Lang, Hana Dvoráková, Jan Cejka
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.
