Synthesis of 6-Trichloromethylphenanthridines by Transition Metal-Free Radical Cyclization of 2-Isocyanobiphenyls.

Synthesis of 6-Trichloromethylphenanthridines by Transition Metal-Free Radical Cyclization of 2-Isocyanobiphenyls.
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DOI:
10.1021/acs.joc.6b00885
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发表时间:
2016-05
期刊:
The Journal of organic chemistry
影响因子:
--
通讯作者:
Yuhan Zhou;Changpeng Wu;Xiaoliang Dong;Jingping Qu
Yuhan Zhou;Changpeng Wu;Xiaoliang Dong;Jingping Qu
中科院分区:
其他
文献类型:
--
作者:
Yuhan Zhou;Changpeng Wu;Xiaoliang Dong;Jingping Qu

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研究了以过氧化苯甲酰为催化剂,2-异氰基联苯与四氯化碳环合合成6-三氯甲基菲啶的方法。提出了一种自由基途径,并证明了反应机理。该反应容许宽范围的官能团,并且所得的6-三氯甲基菲啶可以用作相应的6-取代菲啶的有用的合成前体。
An efficient method for the synthesis of 6-trichloromethylphenanthridines by benzoyl peroxide promoted cyclization reaction of 2-isocyanobiphenyls with carbon tetrachloride is developed. A radical pathway is proposed and evidenced for the reaction mechanism. This reaction tolerates a wide range of functional groups and the resulting 6-trichloromethylphenanthridines can be utilized as a useful synthetic precursor for corresponding 6-substituted phenanthridines.