高等学校化学学报

高等学校化学学报 ›› 1999, Vol. 20 ›› Issue (11): 1733.

• 论文 • 上一篇    下一篇

1,4-二氢Hantzsch吡啶衍生物的合成及其1HNMR和荧光光谱研究

赵炳筠1, 朱晓晴1, 何家骐1, 夏炽中2, 程津培1   

  1. 1. 南开大学化学系, 天津 300071;
    2. 山西大学化学系, 太原 030006
  • 收稿日期:1999-03-12 出版日期:1999-11-24 发布日期:1999-11-24
  • 通讯作者: 程津培
  • 作者简介:赵炳筠,男,30岁,博士研究生.
  • 基金资助:

    国家自然科学基金(批准号:29702005)资助课题

An Investigation on Synthesis and Spectroscopic Properties of Hantzsch Type1,4-Dihydropyridine Derivatives

ZHAO Bing-Jun1, ZHU Xiao-Qing1, HE Jia-Qi1, XIA Chi-Zhong2, CHENG Jin-Pei 1   

  1. 1. Department of Chemistry, Nankai University, Tianjin 300071, China;
    2. Department of Chemistry, Shanxi University, Taiyuan 030006, China
  • Received:1999-03-12 Online:1999-11-24 Published:1999-11-24

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摘要： 报道了N-甲基-4-芳基-2,6-二甲基-3,5-二乙酯基-1,4-二氢吡啶(2a_2f),4-芳基-2,6-二苯基-3,5-二乙酯基-1,4-二氢吡啶(3a_3f)及其相应的N-甲基化合物(4a_4f)的合成(芳基p-RC6H4-;R=OCH3,CH3,H,Cl,CN,NO2).化合物4-芳基-2,6-二甲基-3,5-二乙酯基-1,4-二氢吡啶(1a_1f)可发射较强的荧光,化合物3呈现较弱的荧光,它们的氮甲基产物2和4没有荧光。化合物4氮甲基质子的化学位移值比其相对应的化合物2氮甲基质子的化学位移值向高场移动0.6～0.7.化合物3的4-位次甲基质子的化学位移变化与同碳苯基对位取代基的σP+有相当好的关联。这些现象反映了化合物2-4的特征构象。

关键词: 1, 4-二氢Hantzsch吡啶衍生物, 合成, 1, 4-二氢吡啶环构象, 1HNMR, 荧光光谱

Abstract: Preparation of the Hantzsch type 1,4-dihydropyridine derivatives, i.e. 1,2,6-trimethyl-4-aryl-3,5-dicarbethoxy-1,4 dihydropyridines 2a_2f, 4-aryl -2,6-diphenyl-3,5-dicarbethoxy-1,4-dihydropyridines 3a_3f and their Nmethylated compounds 4a_4f was described(aryl: p-RC6H4-; R=OCH3, CH3, H, Cl, CN, NO2). The 4-aryl-2,6-dimethyl-3,5-dicarbethoxy-1,4-dihydropyridines 1a_1f show a relative strong fluorescence, whereas under the same conditions, compounds 3a_3f give a weak fluorescence. No fluorescence was observed for N-methylated compounds 2a_2f, 4a_4f. In 1HNMR spectra the methyl protons at the 1-position in 4a_4f are shifted unfield by δ= 0.6～0.7 compared to those in 2a_2f. The above observations were rationalized in terms of the conformational changes resulting from the steric interactions among the substitutents in the dihydropyridine ring.

Key words: 1,4-Hantzsch dihydropyridine derivatives, Synthesis, 1,4-Dihydropyridine ring conformation, 1HNMR, Fluoresence spectrum

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