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Bromination of 2-phenyl-1,2,3,4-tetrahydroquinolines
Russian Journal of Organic Chemistry ( IF 0.8 ) Pub Date : 2015-06-26 , DOI: 10.1134/s1070428015050085
M. N. Zemtsova , S. V. Kulemina , V. B. Rybakov , Yu. N. Klimochkin

Bromination of 2-phenyltetrahydroquinolines derivatives was investigated. During the bromination of 2-phenyl-1,2,3,4-tetrahydroquinoline with bromine in chloroform or bromosuccinimide along with the formation of di- and tribrom derivatives the oxidation reaction occurs with the generation of quinoline structure. The interaction of 2-phenyl-1,2,3,4-tetrahydroquinoline with bromine in acetic acid leads to the formation of 6,8-dibromoderivative preserving the 1,2,3,4-tetrahydroquinoline ring. At the same time N-substituted 2-phenyl-1,2,3,4-tetrahydroquinoline is selectively brominated in various conditions with the formation of 6-monobromoderivative. By the method of X-ray diffraction analysis the molecular structure of 3,6,8-tribromo-2-phenylquinoline single crystals was determined.

中文翻译:

2-苯基-1,2,3,4-四氢喹啉的溴化

研究了2-苯基四氢喹啉衍生物的溴化。在2-苯基-1,2,3,4-四氢喹啉与溴在氯仿或溴代琥珀酰亚胺中溴化以及形成二溴和三溴衍生物的过程中,随着喹啉结构的产生,发生了氧化反应。2-苯基-1,2,3,4-四氢喹啉在乙酸中与溴的相互作用导致形成6,8-二溴代衍生物,并保留1,2,3,4-四氢喹啉环。同时,N-取代的2-苯基-1,2,3,4-四氢喹啉在各种条件下被选择性地溴化,形成6-单溴代衍生物。通过X射线衍射分析的方法,确定了3,6,8-三溴-2-苯基喹啉单晶的分子结构。
更新日期:2015-06-26
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