新型氮桥杂环的制备67. α,α'-双[(噻吩并[3,4-b]中氮茚-3-基)硫代]-邻、间和对二甲苯衍生物的合成及其构象结构
Preparation of new nitrogen-bridged heterocycles 67. syntheses of alpha,alpha'-Bis[(thieno[3,4-b]indolizin-3-yl)thio]-o-, m-, and p-xylene derivatives and their conformational structures.
作者信息
Kakehi Akikazu, Suga Hiroyuki, Okumura Yukihisa, Shinohara Masatoshi, Kako Tomonao, Sekiguchi Takeshi, Shiro Motoo
机构信息
Department of Chemistry and Material Engineering, Shinshu University, Wakasato, Nagano, Japan. xkakehi@ shinshu-u.ac.jp
出版信息
Chem Pharm Bull (Tokyo). 2009 Dec;57(12):1385-90. doi: 10.1248/cpb.57.1385.
The alkaline treatment and dehydrogenation of pyridinium salts, formed from the S-alkylations of 3-(1-pyridinio)thiophene-2-thiolates with alpha,alpha-dibromo-o-, m-, or p-xylene, provided the corresponding alpha,alpha'-bis[(thieno[3,4-b]indolizin-3-yl)thio]-o-, m-, and p-xylene derivatives in low to good yields. Both (1)H-NMR and UV-Vis spectra of these products supported distinctly the predominance of the gauche-gauche conformation in relation to the two sulfide linkages as the spacer in these molecules. On the other hand, the X-ray analyses indicated the expected gauche-gauche conformation for the m- and the p-xylene derivatives, but the anti-anti one for the o-xylene derivative.
由3-(1-吡啶基)噻吩-2-硫醇盐与α,α-二溴邻、间或对二甲苯进行S-烷基化反应形成的吡啶盐经碱处理和脱氢反应后，以低至良好的产率得到了相应的α,α'-双[(噻吩并[3,4-b]中氮茚-3-基)硫基]-邻、间和对二甲苯衍生物。这些产物的核磁共振氢谱和紫外-可见光谱均明确支持在这些分子中，作为间隔基的两个硫醚键以邻位交叉-邻位交叉构象占主导。另一方面，X射线分析表明间二甲苯和对二甲苯衍生物具有预期的邻位交叉-邻位交叉构象，但邻二甲苯衍生物为反-反构象。
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