Functionalized 3-(5-aryloxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-1-(4-substituted-phenyl)prop-2-en-1-ones: synthetic pathway, and the structures of six examples
Five examples each of 3-(5-aryloxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-1-[4-(prop-2-yn-1-yloxy)phenyl]prop-2-en-1-ones and the corresponding 1-(4-azidophenyl)-3-(5-aryloxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)prop-2-en-1-ones have been synthesized in a highly efficient manner, starting from a common sou...
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International Union of Crystallography
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doaj-3045cd99c9c84838ac422feaf91c99542020-11-25T02:07:07ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902020-05-0176568369110.1107/S2056989020005113mw2158Functionalized 3-(5-aryloxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-1-(4-substituted-phenyl)prop-2-en-1-ones: synthetic pathway, and the structures of six examplesHaruvegowda Kiran Kumar0Hemmige S. Yathirajan1Asma2Nagaraja Manju3Balakrishna Kalluraya4Ravindranath S. Rathore5Christopher Glidewell6Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru-570 006, IndiaDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru-570 006, IndiaDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore-574199, IndiaDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore-574199, IndiaDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore-574199, IndiaDepartment of Bioinformatics, School of Earth, Biological and Environmental Sciences, Central University of South Bihar, Gaya-824236, IndiaSchool of Chemistry, University of St Andrews, St Andrews, Fife KY16 9ST, UKFive examples each of 3-(5-aryloxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-1-[4-(prop-2-yn-1-yloxy)phenyl]prop-2-en-1-ones and the corresponding 1-(4-azidophenyl)-3-(5-aryloxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)prop-2-en-1-ones have been synthesized in a highly efficient manner, starting from a common source precursor, and structures have been determined for three examples of each type. In each of 3-[5-(2-chlorophenoxy)-3-methyl-1-phenyl-1H-pyrazol-4-yl]-1-[4-(prop-2-yn-1-yloxy)phenyl]prop-2-en-1-one, C28H21ClN2O3, (Ib), the isomeric 3-[5-(2-chlorophenoxy)-3-methyl-1-phenyl-1H-pyrazol-4-yl]-1-[4-(prop-2-yn-1-yloxy)phenyl]prop-2-en-1-one, (Ic), and 3-[3-methyl-5-(naphthalen-2-yloxy)-1-phenyl-1H-pyrazol-4-yl]-1-[4-(prop-2-ynyloxy)phenyl]prop-2-en-1-one, C32H24N2O3, (Ie), the molecules are linked into chains of rings, formed by two independent C—H...O hydrogen bonds in (Ib) and by a combination of C—H...O and C—H...π(arene) hydrogen bonds in each of (Ic) and (Ie). There are no direction-specific intermolecular interactions in the structure of 1-(4-azidophenyl)-3-[3-methyl-5-(2-methylphenoxy)-1-phenyl-1H-pyrazol-4-yl]prop-2-en-1-one, C26H21N5O2, (IIa). In 1-(4-azidophenyl)-3-[5-(2,4-dichlorophenoxy)-3-methyl-1-phenyl-1H-pyrazol-4-yl]prop-2-en-1-one, C25H17Cl2N5O2, (IId), the dichlorophenyl group is disordered over two sets of atomic sites having occupancies 0.55 (4) and 0.45 (4), and the molecules are linked by a single C—H...O hydrogen bond to form cyclic, centrosymmetric R22(20) dimers. Similar dimers are formed in 1-(4-azidophenyl)-3-[3-methyl-5-(naphthalen-2-yloxy)-1-phenyl-1H-pyrazol-4-yl]prop-2-en-1-one, C29H21N5O2, (IIe), but here the dimers are linked into a chain of rings by two independent C—H..π(arene) hydrogen bonds. Comparisons are made between the molecular conformations within both series of compounds.http://scripts.iucr.org/cgi-bin/paper?S2056989020005113synthesissubstituted pyrazoleschalconescrystal structuresdisordermolecular conformationhydrogen bodingsupramolecular assembly |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Haruvegowda Kiran Kumar Hemmige S. Yathirajan Asma Nagaraja Manju Balakrishna Kalluraya Ravindranath S. Rathore Christopher Glidewell |
spellingShingle |
Haruvegowda Kiran Kumar Hemmige S. Yathirajan Asma Nagaraja Manju Balakrishna Kalluraya Ravindranath S. Rathore Christopher Glidewell Functionalized 3-(5-aryloxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-1-(4-substituted-phenyl)prop-2-en-1-ones: synthetic pathway, and the structures of six examples Acta Crystallographica Section E: Crystallographic Communications synthesis substituted pyrazoles chalcones crystal structures disorder molecular conformation hydrogen boding supramolecular assembly |
author_facet |
Haruvegowda Kiran Kumar Hemmige S. Yathirajan Asma Nagaraja Manju Balakrishna Kalluraya Ravindranath S. Rathore Christopher Glidewell |
author_sort |
Haruvegowda Kiran Kumar |
title |
Functionalized 3-(5-aryloxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-1-(4-substituted-phenyl)prop-2-en-1-ones: synthetic pathway, and the structures of six examples |
title_short |
Functionalized 3-(5-aryloxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-1-(4-substituted-phenyl)prop-2-en-1-ones: synthetic pathway, and the structures of six examples |
title_full |
Functionalized 3-(5-aryloxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-1-(4-substituted-phenyl)prop-2-en-1-ones: synthetic pathway, and the structures of six examples |
title_fullStr |
Functionalized 3-(5-aryloxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-1-(4-substituted-phenyl)prop-2-en-1-ones: synthetic pathway, and the structures of six examples |
title_full_unstemmed |
Functionalized 3-(5-aryloxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-1-(4-substituted-phenyl)prop-2-en-1-ones: synthetic pathway, and the structures of six examples |
title_sort |
functionalized 3-(5-aryloxy-3-methyl-1-phenyl-1h-pyrazol-4-yl)-1-(4-substituted-phenyl)prop-2-en-1-ones: synthetic pathway, and the structures of six examples |
publisher |
International Union of Crystallography |
series |
Acta Crystallographica Section E: Crystallographic Communications |
issn |
2056-9890 |
publishDate |
2020-05-01 |
description |
Five examples each of 3-(5-aryloxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-1-[4-(prop-2-yn-1-yloxy)phenyl]prop-2-en-1-ones and the corresponding 1-(4-azidophenyl)-3-(5-aryloxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)prop-2-en-1-ones have been synthesized in a highly efficient manner, starting from a common source precursor, and structures have been determined for three examples of each type. In each of 3-[5-(2-chlorophenoxy)-3-methyl-1-phenyl-1H-pyrazol-4-yl]-1-[4-(prop-2-yn-1-yloxy)phenyl]prop-2-en-1-one, C28H21ClN2O3, (Ib), the isomeric 3-[5-(2-chlorophenoxy)-3-methyl-1-phenyl-1H-pyrazol-4-yl]-1-[4-(prop-2-yn-1-yloxy)phenyl]prop-2-en-1-one, (Ic), and 3-[3-methyl-5-(naphthalen-2-yloxy)-1-phenyl-1H-pyrazol-4-yl]-1-[4-(prop-2-ynyloxy)phenyl]prop-2-en-1-one, C32H24N2O3, (Ie), the molecules are linked into chains of rings, formed by two independent C—H...O hydrogen bonds in (Ib) and by a combination of C—H...O and C—H...π(arene) hydrogen bonds in each of (Ic) and (Ie). There are no direction-specific intermolecular interactions in the structure of 1-(4-azidophenyl)-3-[3-methyl-5-(2-methylphenoxy)-1-phenyl-1H-pyrazol-4-yl]prop-2-en-1-one, C26H21N5O2, (IIa). In 1-(4-azidophenyl)-3-[5-(2,4-dichlorophenoxy)-3-methyl-1-phenyl-1H-pyrazol-4-yl]prop-2-en-1-one, C25H17Cl2N5O2, (IId), the dichlorophenyl group is disordered over two sets of atomic sites having occupancies 0.55 (4) and 0.45 (4), and the molecules are linked by a single C—H...O hydrogen bond to form cyclic, centrosymmetric R22(20) dimers. Similar dimers are formed in 1-(4-azidophenyl)-3-[3-methyl-5-(naphthalen-2-yloxy)-1-phenyl-1H-pyrazol-4-yl]prop-2-en-1-one, C29H21N5O2, (IIe), but here the dimers are linked into a chain of rings by two independent C—H..π(arene) hydrogen bonds. Comparisons are made between the molecular conformations within both series of compounds. |
topic |
synthesis substituted pyrazoles chalcones crystal structures disorder molecular conformation hydrogen boding supramolecular assembly |
url |
http://scripts.iucr.org/cgi-bin/paper?S2056989020005113 |
work_keys_str_mv |
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