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...
| Main Authors: | , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
International Union of Crystallography
2020-05-01
|
| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989020005113 |
| _version_ | 1818914662165512192 |
|---|---|
| author | Haruvegowda Kiran Kumar Hemmige S. Yathirajan Asma Nagaraja Manju Balakrishna Kalluraya Ravindranath S. Rathore Christopher Glidewell |
| author_facet | Haruvegowda Kiran Kumar Hemmige S. Yathirajan Asma Nagaraja Manju Balakrishna Kalluraya Ravindranath S. Rathore Christopher Glidewell |
| author_sort | Haruvegowda Kiran Kumar |
| collection | DOAJ |
| 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. |
| first_indexed | 2024-12-19T23:49:57Z |
| format | Article |
| id | doaj.art-3045cd99c9c84838ac422feaf91c9954 |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-12-19T23:49:57Z |
| publishDate | 2020-05-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-3045cd99c9c84838ac422feaf91c99542022-12-21T20:01:11ZengInternational 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 |
| 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 |
| 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_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_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_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 |
| 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 | AT haruvegowdakirankumar functionalized35aryloxy3methyl1phenyl1hpyrazol4yl14substitutedphenylprop2en1onessyntheticpathwayandthestructuresofsixexamples AT hemmigesyathirajan functionalized35aryloxy3methyl1phenyl1hpyrazol4yl14substitutedphenylprop2en1onessyntheticpathwayandthestructuresofsixexamples AT asma functionalized35aryloxy3methyl1phenyl1hpyrazol4yl14substitutedphenylprop2en1onessyntheticpathwayandthestructuresofsixexamples AT nagarajamanju functionalized35aryloxy3methyl1phenyl1hpyrazol4yl14substitutedphenylprop2en1onessyntheticpathwayandthestructuresofsixexamples AT balakrishnakalluraya functionalized35aryloxy3methyl1phenyl1hpyrazol4yl14substitutedphenylprop2en1onessyntheticpathwayandthestructuresofsixexamples AT ravindranathsrathore functionalized35aryloxy3methyl1phenyl1hpyrazol4yl14substitutedphenylprop2en1onessyntheticpathwayandthestructuresofsixexamples AT christopherglidewell functionalized35aryloxy3methyl1phenyl1hpyrazol4yl14substitutedphenylprop2en1onessyntheticpathwayandthestructuresofsixexamples |