|
|Section2= |Section3= }} Phenanthridine is a nitrogen heterocyclic compound that is the basis of DNA-binding fluorescent dyes through intercalation. Examples of such dyes are ethidium bromide and propidium iodide. Acridine is an isomer of phenanthridine. Phenanthridine was discovered by Amé Pictet and H. J. Ankersmit in 1891 by pyrolysis of the condensation product of benzaldehyde and aniline.〔''Mittheilung Ueber das Phenanthridin '' Amé Pictet, H. J. Ankersmit Chemisches Laboratorium der Universität Genf Justus Liebigs Annalen der Chemie Volume 266 Issue 1-2, pp. 138–153 〕 In the Pictet–Hubert reaction (1899) the compound is formed in a reaction of the 2-aminobiphenyl – formaldehyde adduct (an ''N''-acyl-''o''-xenylamine) with zinc chloride at elevated temperatures.〔''Mittheilungen Ueber eine neue Synthese der Phenanthridinbasen'' Amé Pictet, A. Hubert Berichte der deutschen chemischen Gesellschaft Volume 29 Issue 2, pp. 1182–1189, 1896 〕 The reaction conditions for the Pictet–Hubert reaction were improved by Morgan and Walls in 1931, replacing the metal by phosphorus oxychloride and using nitrobenzene as a reaction solvent.〔''CCCXXXV.—Researches in the phenanthridine series. Part I. A new synthesis of phenanthridine homologues and derivatives'' Gilbert T. Morgan, Leslie Percy Walls, J. Chem. Soc., 1931, 2447–2456 〕 For this reason, the reaction is also called the Morgan–Walls reaction.〔Jie Jack Li (ed.), 2004, ''Name Reactions in Heterocyclic Chemistry'', Wiley.〕 : The reaction is similar to the Bischler–Napieralski reaction and the Pictet–Spengler reaction. ==References== 抄文引用元・出典: フリー百科事典『 ウィキペディア（Wikipedia）』 ■ウィキペディアで「phenanthridine」の詳細全文を読む スポンサード リンク
|