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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

Compounds (I), C(22)H(20)N(2)O(2), (II), C(22)H(20)N(2)O(2) and (III), C(20)H(18)N(2)O(3) 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...

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Autores principales: Zaytsev, Vladimir P., Sorokina, Elena A., Kvyatkovskaya, Elisaveta A., Toze, Flavien A. A., Mhaldar, Shashank N., Dorovatovskii, Pavel V., Khrustalev, Victor N.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2018
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Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6072988/
https://www.ncbi.nlm.nih.gov/pubmed/30116571
http://dx.doi.org/10.1107/S2056989018009982
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author Zaytsev, Vladimir P.
Sorokina, Elena A.
Kvyatkovskaya, Elisaveta A.
Toze, Flavien A. A.
Mhaldar, Shashank N.
Dorovatovskii, Pavel V.
Khrustalev, Victor N.
author_facet Zaytsev, Vladimir P.
Sorokina, Elena A.
Kvyatkovskaya, Elisaveta A.
Toze, Flavien A. A.
Mhaldar, Shashank N.
Dorovatovskii, Pavel V.
Khrustalev, Victor N.
author_sort Zaytsev, Vladimir P.
collection PubMed
description Compounds (I), C(22)H(20)N(2)O(2), (II), C(22)H(20)N(2)O(2) and (III), C(20)H(18)N(2)O(3) 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 P2(1)/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.
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spelling pubmed-60729882018-08-16 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 Zaytsev, Vladimir P. Sorokina, Elena A. Kvyatkovskaya, Elisaveta A. Toze, Flavien A. A. Mhaldar, Shashank N. Dorovatovskii, Pavel V. Khrustalev, Victor N. Acta Crystallogr E Crystallogr Commun Research Communications Compounds (I), C(22)H(20)N(2)O(2), (II), C(22)H(20)N(2)O(2) and (III), C(20)H(18)N(2)O(3) 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 P2(1)/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. International Union of Crystallography 2018-07-13 /pmc/articles/PMC6072988/ /pubmed/30116571 http://dx.doi.org/10.1107/S2056989018009982 Text en © Zaytsev et al. 2018 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/2.0/uk/
spellingShingle Research Communications
Zaytsev, Vladimir P.
Sorokina, Elena A.
Kvyatkovskaya, Elisaveta A.
Toze, Flavien A. A.
Mhaldar, Shashank N.
Dorovatovskii, Pavel V.
Khrustalev, Victor N.
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
title 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
title_full 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
title_fullStr 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
title_full_unstemmed 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
title_short 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
title_sort 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
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6072988/
https://www.ncbi.nlm.nih.gov/pubmed/30116571
http://dx.doi.org/10.1107/S2056989018009982
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