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Two new 1-(thia-zol-2-yl)-4,5-di-hydropyrazoles have been synthesized from simple precursors, and characterized both spectroscopically and structurally. In addition, two inter-mediates in the reaction pathway have been isolated and characterized, one of them structurally. The mol-ecules of the inter-mediate ( E )-1-(4-meth-oxy-phen-yl)-3-[4-(prop-2-yn-yloxy)phen-yl]prop-2-en-1-one, C 19 H 16 O 3 (I), are linked by a combination of C-H⋯O and C-H⋯π(arene) hydrogen bonds to form ribbons. The products ( RS )-5-(4-meth-oxy-phen-yl)-1-(4-phenythiazol-2-yl)-3-[4-(prop-2-yn--yloxy)phen-yl]-4,5-di-hydro-1 H -pyrazole, C 28 H 23 N 3 O 2 S (II), and ( RS )-5-(4-meth-oxy-phen-yl)-1-[4-(4-methyl-phen-yl)thia-zol-2-yl]-3-[4-(prop-2-yn-yloxy)phen-yl]-4,5-di-hydro-1 H -pyrazole, C 29 H 25 N 3 O 2 S (III), are closely related - differing only by presence or absence of a methyl group at the aryl-thia-zolyl substituent - and crystallize in an isomorphous setting. Both mol-ecules contain an effectively planar di-hydro-pyrazole ring, and possess an overall T-shaped structure, which is a characteristic of triaryl-substituted 4,5-di-hydro-1-(thia-zol-2-yl)pyrazole compounds. The crystal packing is characterized by inter-molecular C-H⋯S and C-H⋯π (ar-yl/alkyne) inter-actions. A combination of two C-H⋯π(arene) hydrogen bonds links the product mol-ecules into sheets.

acta crystallographica. section e, crystallographic communications

Formation of 1-(thiazol-2-yl)-4,5-dihydropyrazoles from simple precursors: synthesis, spectroscopic characterization and the structures of an intermediate and two products