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

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2 Citations (Scopus)

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 languageEnglish
Pages (from-to)683-691
Number of pages9
JournalActa Crystallographica Section E Crystallographic Communications
Volume76
Issue number5
Early online date21 Apr 2020
DOIs
Publication statusPublished - 1 May 2020

Keywords

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

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