Three-component reaction between isatoic anhydride, amine and methyl-substituted furylacrylaldehydes: crystal structures of 3-benzyl-2-[(E)-2-(5-methylfuran-2-yl)vinyl]-2,3-dihydroquinazolin-4(1H)-one, 3-benzyl-2-[(E)-2-(furan-2-yl)-1-methylvinyl]-2,3-dihydroquinazolin-4(1H)-one and 3-(furan-2-ylmethyl)-2-[(E)-2-(furan-2-yl)-1-methylvinyl]-2,3-dihydroquinazolin-4(1H)-one

Abstract

Compounds (I), C22H20N2O2, (II), C22H20N2O2 and (III), C20H18N2O3 are the products of three-component reactions between isatoic anhydride, the corresponding amine and 3-(5-methylfuran-2-yl)- or (furan-2-yl)-2-methylacrylaldehyde. Compound (I) crystallizes in the monoclinic space group P21/n, while compounds (II) and (III) are isostructural and crystallize in the orthorhombic space group Pbca. The tetrahydropyrimidine ring in (I)–(III) adopts a sofa conformation. The NH nitrogen atom has a trigonal–pyramidal geometry, whereas the N(R) nitrogen atom is flattened. The furyl-vinyl substituents in (I)–(III) are practically planar and have an E configuration at the C=C double bond. In (I), this bulky fragment occupies the axial position at the quaternary carbon atom of the tetrahydropyrimidine ring, whereas in (II) and (III) it is equatorially disposed. In the crystal of (I), molecules form hydrogen-bonded chains propagating along [001] by strong intermolecular N—H...O hydrogen bonds. The chains are packed in stacks along the a-axis direction. In the crystals of (II) and (III), molecules also form hydrogen-bonded chains propagating along [100] by strong intermolecular N—H...O hydrogen bonds. However, despite the fact that compounds (II) and (III) are isostructural, steric differences between the phenyl and furyl substituents result in chains with different geometries. Thus in the crystal of (II) the chains have a zigzag-like structure, whereas in the crystal of (III), they are almost linear. In both (II) and (III), the hydrogen-bonded chains are further packed in stacks along the b-axis direction.

Keywords

• furans
• quinazolinones
• acid anhydrides
• three-component reaction
• crystal structure
• synchrotron radiation