2-异氰基联苯的无过渡金属自由基环化合成 6-三氯甲基菲啶

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

机构信息

State Key Laboratory of Fine Chemicals, School of Pharmaceutical Science and Technology, Dalian University of Technology , Dalian 116024, P.R. China.

出版信息

J Org Chem. 2016 Jun 17;81(12):5202-8. doi: 10.1021/acs.joc.6b00885. Epub 2016 May 31.

DOI:10.1021/acs.joc.6b00885

PMID:27218656

Abstract

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.

摘要

发展了过氧化苯甲酰促进 2-异氰基联苯与四氯化碳环化反应合成 6-三氯甲基菲啶的有效方法。提出并证实了该反应的自由基途径。该反应可耐受广泛的官能团，得到的 6-三氯甲基菲啶可作为相应 6-取代菲啶的有用合成前体。