Crystal structure of 3-benzyl-2-[(E)-2-(furan-2-yl)ethenyl]-2,3-dihydroquinazolin-4(1H)-one and 3-benzyl-2-[(E)-2-(thiophen-2-yl)ethenyl]-2,3-dihydroquinazolin-4(1H)-one from synchrotron X-ray diffraction

The chiral title compounds, C21H18N2O2, (I), and C21H18N2OS, (II) - products of the three-component reaction between benzylamine, isatoic anhydride and furyl- or thienyl-acrolein - are isostructural and form isomorphous racemic crystals. The tetrahydropyrimidine 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 tetrahydropyrimidine ring, apparently, due to steric reasons. In the crystals, molecules of (I) and (II) form hydrogen-bonded helicoidal chains propagating along [010] by strong intermolecular N - H⋯O hydrogen bonds. © Toze et al. 2018.

Авторы
Редакторы
-
Издательство
International Union of Crystallography
Номер выпуска
-
Язык
Английский
Страницы
10-14
Статус
Опубликовано
Подразделение
-
Номер
-
Том
74
Год
2018
Организации
  • 1 Department of Chemistry, Faculty of Sciences, University of Douala, PO Box 24157, Douala, 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
Ключевые слова
2-ethenylquinazolines; crystal structure; furyl-acrolein; synchrotron radiation; thienyl-acrolein; three-component reaction
Дата создания
19.10.2018
Дата изменения
19.10.2018
Постоянная ссылка
https://repository.rudn.ru/ru/records/article/record/7289/