Functionalized 3-(5-ar-yloxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-1-(4-substituted-phen-yl)prop-2-en-1-ones: synthetic pathway, and the structures of six examples

Haruvegowda Kiran Kumar; Hemmige S Yathirajan; null Asma; Nagaraja Manju; Balakrishna Kalluraya; Ravindranath S Rathore; Christopher Glidewell

doi:10.1107/S2056989020005113

Functionalized 3-(5-ar-yloxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-1-(4-substituted-phen-yl)prop-2-en-1-ones: synthetic pathway, and the structures of six examples

Haruvegowda Kiran Kumar, Hemmige S Yathirajan, Asma, Nagaraja Manju, Balakrishna Kalluraya, Ravindranath S Rathore, Christopher Glidewell

School of Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

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.

Original language	English
Pages (from-to)	683-691
Number of pages	9
Journal	Acta Crystallographica Section E Crystallographic Communications
Volume	76
Issue number	5
Early online date	21 Apr 2020
DOIs	https://doi.org/10.1107/S2056989020005113
Publication status	Published - 1 May 2020

Keywords

Synthesis
Substitued pyrazoles
Chalcones
Crystal structures
Disorder
Molecular conformation
Hydrogen bonding
Supramolecular assembly

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Copyright © 2020 The Author(s). 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.
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CCDC 1996402 - 1996407: Experimental Crystal Structure Determination
Kumar, H. K. (Contributor), Yathirajan, H. S. (Contributor), Asma (Contributor), Manju, N. (Contributor), Kalluraya, B. (Contributor), Rathore, R. S. (Contributor) & Glidewell, C. (Contributor), The Cambridge Structural Database, 11 Apr 2020
DOI: 10.5517/ccdc.csd.cc250f7w, https://dx.doi.org/10.5517/ccdc.csd.cc250f6v and 4 more links, https://dx.doi.org/10.5517/ccdc.csd.cc250f5t, https://dx.doi.org/10.5517/ccdc.csd.cc250f4s, https://dx.doi.org/10.5517/ccdc.csd.cc250f3r, https://dx.doi.org/10.5517/ccdc.csd.cc250f2q (show fewer)
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Kiran Kumar, H., Yathirajan, H. S., Asma, Manju, N., Kalluraya, B., Rathore, R. S., & Glidewell, C. (2020). Functionalized 3-(5-ar-yloxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-1-(4-substituted-phen-yl)prop-2-en-1-ones: synthetic pathway, and the structures of six examples. Acta Crystallographica Section E Crystallographic Communications, 76(5), 683-691. https://doi.org/10.1107/S2056989020005113

@article{efc7241980ef4f12a0778bf736307185,

title = "Functionalized 3-(5-ar-yloxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-1-(4-substituted-phen-yl)prop-2-en-1-ones: synthetic pathway, and the structures of six examples",

abstract = "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.",

keywords = "Synthesis, Substitued pyrazoles, Chalcones, Crystal structures, Disorder, Molecular conformation, Hydrogen bonding, Supramolecular assembly",

author = "{Kiran Kumar}, Haruvegowda and Yathirajan, {Hemmige S} and Asma and Nagaraja Manju and Balakrishna Kalluraya and Rathore, {Ravindranath S} and Christopher Glidewell",

note = "HSY thanks the University Grants Commission, New Delhi for the award of a BSR Faculty Fellowship for three years.",

year = "2020",

month = may,

day = "1",

doi = "10.1107/S2056989020005113",

language = "English",

volume = "76",

pages = "683--691",

journal = "Acta Crystallographica Section E Crystallographic Communications",

issn = "2056-9890",

publisher = "International Union of Crystallography",

number = "5",

}

Kiran Kumar, H, Yathirajan, HS, Asma, Manju, N, Kalluraya, B, Rathore, RS & Glidewell, C 2020, 'Functionalized 3-(5-ar-yloxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-1-(4-substituted-phen-yl)prop-2-en-1-ones: synthetic pathway, and the structures of six examples', Acta Crystallographica Section E Crystallographic Communications, vol. 76, no. 5, pp. 683-691. https://doi.org/10.1107/S2056989020005113

Functionalized 3-(5-ar-yloxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-1-(4-substituted-phen-yl)prop-2-en-1-ones: synthetic pathway, and the structures of six examples. / Kiran Kumar, Haruvegowda; Yathirajan, Hemmige S; Asma et al.
In: Acta Crystallographica Section E Crystallographic Communications, Vol. 76, No. 5, 01.05.2020, p. 683-691.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Functionalized 3-(5-ar-yloxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-1-(4-substituted-phen-yl)prop-2-en-1-ones

T2 - synthetic pathway, and the structures of six examples

AU - Kiran Kumar, Haruvegowda

AU - Yathirajan, Hemmige S

AU - Asma, null

AU - Manju, Nagaraja

AU - Kalluraya, Balakrishna

AU - Rathore, Ravindranath S

AU - Glidewell, Christopher

N1 - HSY thanks the University Grants Commission, New Delhi for the award of a BSR Faculty Fellowship for three years.

PY - 2020/5/1

Y1 - 2020/5/1

N2 - 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.

AB - 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.

KW - Synthesis

KW - Substitued pyrazoles

KW - Chalcones

KW - Crystal structures

KW - Disorder

KW - Molecular conformation

KW - Hydrogen bonding

KW - Supramolecular assembly

U2 - 10.1107/S2056989020005113

DO - 10.1107/S2056989020005113

M3 - Article

C2 - 32431933

SN - 2056-9890

VL - 76

SP - 683

EP - 691

JO - Acta Crystallographica Section E Crystallographic Communications

JF - Acta Crystallographica Section E Crystallographic Communications

IS - 5

ER -

Kiran Kumar H, Yathirajan HS, Asma, Manju N, Kalluraya B, Rathore RS et al. Functionalized 3-(5-ar-yloxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-1-(4-substituted-phen-yl)prop-2-en-1-ones: synthetic pathway, and the structures of six examples. Acta Crystallographica Section E Crystallographic Communications. 2020 May 1;76(5):683-691. Epub 2020 Apr 21. doi: 10.1107/S2056989020005113

Functionalized 3-(5-ar-yloxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-1-(4-substituted-phen-yl)prop-2-en-1-ones: synthetic pathway, and the structures of six examples

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CCDC 1996402 - 1996407: Experimental Crystal Structure Determination

Cite this