Crystal structure of 3-benzyl-2-[(E)-2-(furan-2-yl)ethen-yl]-2,3-di-hydro-quinazolin-4(1 H)-one and 3-benzyl-2-[(E)-2-(thio-phen-2-yl)ethen-yl]-2,3-di-hydro-quinazolin-4(1 H)-one from synchrotron X-ray diffraction

Flavien A A Toze; Vladimir P Zaytsev; Lala V Chervyakova; Elisaveta A Kvyatkovskaya; Pavel V Dorovatovskii; Victor N Khrustalev

doi:10.1107/S2056989017017479

Crystal structure of 3-benzyl-2-[(E)-2-(furan-2-yl)ethen-yl]-2,3-di-hydro-quinazolin-4(1 H)-one and 3-benzyl-2-[(E)-2-(thio-phen-2-yl)ethen-yl]-2,3-di-hydro-quinazolin-4(1 H)-one from synchrotron X-ray diffraction

Acta Crystallogr E Crystallogr Commun. 2018 Jan 1;74(Pt 1):10-14. doi: 10.1107/S2056989017017479.

Authors

Flavien A A Toze¹, Vladimir P Zaytsev², Lala V Chervyakova², Elisaveta A Kvyatkovskaya², Pavel V Dorovatovskii³, Victor N Khrustalev⁴

Affiliations

¹ Department of Chemistry, Faculty of Sciences, University of Douala, PO Box 24157, Douala, Republic of Cameroon.
² Organic Chemistry Department, Peoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklay St., Moscow 117198, Russian Federation.
³ National Research Centre "Kurchatov Institute", 1 Acad. Kurchatov Sq., Moscow 123182, Russian Federation.
⁴ Inorganic Chemistry Department, Peoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklay St., Moscow 117198, Russian Federation.

Abstract

The chiral title compounds, C₂₁H₁₈N₂O₂, (I), and C₂₁H₁₈N₂OS, (II) - products of the three-component reaction between benzyl-amine, isatoic anhydride and furyl- or thienyl-acrolein - are isostructural and form isomorphous racemic crystals. The tetra-hydro-pyrimidine ring in (I) and (II) adopts a sofa conformation. The amino N atom has a trigonal-pyramidal geometry [sum of the bond angles is 347.0° for both (I) and (II)], whereas the amido N atom is flat [sum of the bond angles is 359.3° for both (I) and (II)]. The furyl- and thienylethenyl substituents in (I) and (II) are planar and the conformation about the bridging C=C bond is E. These bulky fragments occupy the axial position at the quaternary C atom of the tetra-hydro-pyrimidine ring, apparently, due to steric reasons. In the crystals, mol-ecules of (I) and (II) form hydrogen-bonded helicoidal chains propagating along [010] by strong inter-molecular N-H⋯O hydrogen bonds.

Keywords: 2-ethenylquinazolines; crystal structure; furyl-acrolein; synchrotron radiation; thienyl-acrolein; three-component reaction.

Grants and funding

This work was funded by Ministry of Education and Science of the Russian Federation grant 4.1154.2017/4.6. Russian Foundation for Basic Research grant 16–03-00125.