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-methyl-acryl-aldehyde. Compound (I) crystallizes in the monoclinic space group P21/n, while compounds (II) and (III) are isostructural and crystallize in the ortho-rhom-bic space group Pbca. The tetra-hydro-pyrimidine ring in (I)-(III) adopts a sofa conformation. The NH nitro-gen atom has a trigonal-pyramidal geometry, whereas the N(R) nitro-gen 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 tetra-hydro-pyrimidine ring, whereas in (II) and (III) it is equatorially disposed. In the crystal of (I), mol-ecules form hydrogen-bonded chains propagating along [001] by strong inter-molecular N-H⋯O hydrogen bonds. The chains are packed in stacks along the a-axis direction. In the crystals of (II) and (III), mol-ecules also form hydrogen-bonded chains propagating along [100] by strong inter-molecular 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.
Highlights
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-2-methylacrylaldehyde
Only one example of the synthesis of 3-(furyl)allylamines linked to a quinazoline fragment has been described in literature (Zaytsev et al, 2015). 2-Vinylfurylquinazolinones containing no methyl groups were obtained by a three-component reaction between isatoic anhydride, a primary amine, and furylacrolein
Some further transformation of these quinazolinones has been demonstrated. This communication pursues the aim of acquiring structural information about 2-vinylfurylquinazolinones bearing a methyl group on the furan ring or at the double bond of the allylamine fragment, with the aim of further elucidating all aspects of its interaction with, -unsaturated acid anhydrides
Summary
3-Aryl- and 3-hetaryl-substituted allylamines and allylic alcohols are readily available and are common starting materials for the synthesis of complex cyclic systems with useful properties (Frackenpohl et al, 2016; Celltech R&D Ltd, 2004).
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