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

Five examples each of 3-(5-ar-yloxy-3-methyl-1-phenyl-1 -pyrazol-4-yl)-1-[4-(prop-2-yn-1-yl-oxy)phen-yl]prop-2-en-1-ones and the corresponding 1-(4-azido-phen-yl)-3-(5-ar-yloxy-3-methyl-1-phenyl-1 -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-chloro-phen-oxy)-3-methyl-1-phenyl-1 -pyrazol-4-yl]-1-[4-(prop-2-yn-1-yl-oxy)phen-yl]prop-2-en-1-one, C H ClN O , (Ib), the isomeric 3-[5-(2-chloro-phen-oxy)-3-methyl-1-phenyl-1 -pyrazol-4-yl]-1-[4-(prop-2-yn-1-yl-oxy)phen-yl]prop-2-en-1-one, (Ic), and 3-[3-methyl-5-(naphthalen-2-yl-oxy)-1-phenyl-1 -pyrazol-4-yl]-1-[4-(prop-2-yn-yloxy)phen-yl]prop-2-en-1-one, C H N O , (Ie), the mol-ecules 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 inter-molecular inter-actions in the structure of 1-(4-azido-phen-yl)-3-[3-methyl-5-(2-methyl-phen-oxy)-1-phenyl-1 -pyrazol-4-yl]prop-2-en-1-one, C H N O , (IIa). In 1-(4-azido-phen-yl)-3-[5-(2,4-di-chloro-phen-oxy)-3-methyl-1-phenyl-1 -pyrazol-4-yl]prop-2-en-1-one, C H Cl N O , (IId), the di-chloro-phenyl group is disordered over two sets of atomic sites having occupancies 0.55 (4) and 0.45 (4), and the mol-ecules are linked by a single C-H⋯O hydrogen bond to form cyclic, centrosymmetric (20) dimers. Similar dimers are formed in 1-(4-azido-phen-yl)-3-[3-methyl-5-(naphthalen-2-yl-oxy)-1-phenyl-1 -pyrazol-4-yl]prop-2-en-1-one, C H N O , (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 mol-ecular conformations within both series of compounds.