Heterocyclic 3,5-disubstituted phenylpyrazoles and isoxazoles: synthesis and mesomorphic behavior

被引：18
作者：
Kuo, Hsiu-Ming [1 ]
Tsai, Shao-Ling [1 ]
Lee, Gene-Hsiang [2 ]
Sheu, Hwo-Shuenn [3 ]
Lai, Chung K. [1 ]
机构：
[1] Natl Cent Univ, Dept Chem, Chungli 32001, Taiwan
[2] Natl Taiwan Univ, Instrumentat Ctr, Taipei 10660, Taiwan
[3] Natl Synchrotron Radiat Res Ctr, Hsinchu 30077, Taiwan
来源：
TETRAHEDRON | 2013年 / 69卷 / 02期
关键词：
LIQUID-CRYSTALLINE; ALLYLPALLADIUM COMPLEXES; PYRAZOLE; DERIVATIVES; LIGANDS;
D O I：
10.1016/j.tet.2012.11.013
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Three new series of heterocyclic pyrazoles Mpz-C-n and Epz-C-n and isoxazoles Iz-C-n were prepared, characterized, and their mesomorphic properties investigated. These heterocyclic derivatives were obtained by condensation-cyclization of beta-diketones with methylhydrazine, 2-hydradinoethanol or hydroxylamine in refluxing THF/ethanol. One single crystallographic structure of nonmesogenic Epz-C-4 was determined by X-ray analysis. It crystallizes in a triclinic space group P-1. An H-bond-induced structure was formed, giving a better aspect ratio required for the formation of mesophases. Both series of pyrazoles Mpz-C-n and EpZ-C-n exhibited monotropic smectic A phases, in contrast, isoxazoles Iz-C-n formed enantiotropic smectic C phases. A lack of H-bond due to a removal of hydrogen atom from pyrazolyl rings (-NH) significantly lowered the clearing temperatures of both Mpz-C-n and EpZ-C-n. These compounds have good thermal stabilities. (c) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码：618 / 626
页数：9
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