Mahesha Ninganayaka, Yathirajan Hemmige S, Nagma Banu Holalagudu A, Kalluraya Balakrishna, Rathore Ravindranath S, Glidewell Christopher
Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru-570 006, India.
Department of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore-574199, India.
Acta Crystallogr E Crystallogr Commun. 2021 Sep 10;77(Pt 10):975-981. doi: 10.1107/S2056989021009312. eCollection 2021 Oct 1.
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 ()-1-(4-meth-oxy-phen-yl)-3-[4-(prop-2-yn-yloxy)phen-yl]prop-2-en-1-one, CHO (I), are linked by a combination of C-H⋯O and C-H⋯π(arene) hydrogen bonds to form ribbons. The products ()-5-(4-meth-oxy-phen-yl)-1-(4-phenythiazol-2-yl)-3-[4-(prop-2-yn--yloxy)phen-yl]-4,5-di-hydro-1-pyrazole, CHNOS (II), and ()-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-pyrazole, CHNOS (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.
由简单前体合成了两种新型1-(噻唑-2-基)-4,5-二氢吡唑，并通过光谱和结构表征。此外，分离并表征了反应途径中的两种中间体，其中一种进行了结构表征。中间体()-1-(4-甲氧基苯基)-3-[4-(丙-2-炔氧基)苯基]丙-2-烯-1-酮（CHO，I）的分子通过C-H⋯O和C-H⋯π(芳烃)氢键的组合连接形成带状结构。产物()-5-(4-甲氧基苯基)-1-(4-苯基噻唑-2-基)-3-[4-(丙-2-炔氧基)苯基]-4,5-二氢-1-吡唑（CHNOS，II）和()-5-(4-甲氧基苯基)-1-[4-(4-甲基苯基)噻唑-2-基]-3-[4-(丙-2-炔氧基)苯基]-4,5-二氢-1-吡唑（CHNOS，III）密切相关——仅在芳基噻唑基取代基处是否存在甲基上有所不同——并在同构环境中结晶。两种分子都含有一个有效平面的二氢吡唑环，并具有整体T形结构，这是三芳基取代的4,5-二氢-1-(噻唑-2-基)吡唑化合物的特征。晶体堆积的特征是分子间C-H⋯S和C-H⋯π(芳基/炔烃)相互作用。两个C-H⋯π(芳烃)氢键的组合将产物分子连接成片层。
