Three-component reaction between isatoic anhydride, amine and meth-yl-subs-tituted furyl-acryl-alde-hydes: Crystal structures of 3-benzyl-2-[(E)-2-(5-methylfuran-2-yl)vin-yl]-2,3-di-hydro-quinazolin-4(1 H)-one, 3-benzyl-2-[(E)-2-(furan-2-yl)-1-methyl-vin-yl]-2,3-di-hydro-quinazolin-4(1 H)-one and 3-(furan-2-ylmeth-yl)-2-[(E)-2-(furan-2-yl)-1-methyl-vin-yl]-2,3-di-hydro-quinazolin-4(1 H)-one

Compounds (I), C22 H20 N2 O2, (II), C22 H20 N2 O2 and (III), C20 H18 N2 O3 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 P2 1 /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. © 2018 Zaytsev et al.

Авторы
Zaytsev V.P. 1 , Sorokina E.A. 1 , Kvyatkovskaya E.A. 1 , Toze F.A.A. 2 , Mhaldar S.N.3 , Dorovatovskii P.V.4 , Khrustalev V.N. 4, 5
Редакторы
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Издательство
International Union of Crystallography
Номер выпуска
-
Язык
Английский
Страницы
1101-1106
Статус
Опубликовано
Подразделение
-
Номер
-
Том
74
Год
2018
Организации
  • 1 Organic Chemistry Department, Peoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklay St., Moscow, 117198, Russian Federation
  • 2 Department of Chemistry, Faculty of Sciences, University of Douala, PO Box 24157, Douala, Cameroon
  • 3 Department of Chemistry, Goa University, Taleigao Plateau, Goa, 403 206, India
  • 4 National Research Centre kurchatov Institute, 1 Acad. Kurchatov Sq., Moscow, 123182, Russian Federation
  • 5 Inorganic Chemistry Department, Peoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklay St., Moscow, 117198, Russian Federation
Ключевые слова
acid anhydrides; crystal structure; furans; quinazolinones; synchrotron radiation; three-component reaction
Дата создания
19.10.2018
Дата изменения
19.10.2018
Постоянная ссылка
https://repository.rudn.ru/ru/records/article/record/7188/