Double anionic cycloaromatization of 2-(6-substituted-3-hexene-1,5-diynyl)benzonitriles initiated by methoxide addition.
[reaction: see text] Treatment of 2-((3Z)-undecene-1,5-diynyl)benzonitrile with 5 equiv of sodium methoxide in refluxing methanol for 16 h gave 1-pentyl-6-methoxyphenanthridine in 12% yield, 1-pentyl-6-phenanthridone in 6% yield, and 2-(2-pentyl-6-methoxyphenyl)benzonitrile in 4% yield. Under the same reaction conditions, methanolysis of several other benzonitriles gave similar results. Phenanthridine and biphenyl derivatives were obtained as the major products. A mechanism for this novel cycloaromatization reaction of enediynes is proposed.
Wu
M J
MJ
School of Chemistry, Kaohsiung Medical College, Kaohsiung, Taiwan. mijuwu@cc.kmc.edu.tw
Lin
C F
CF
Chen
S H
SH
D003500:Cyclization; D006841:Hydrocarbons, Aromatic / Q000138:chemical synthesis; D007202:Indicators and Reagents; D009570:Nitriles / Q000138:chemical synthesis*
D006841:Hydrocarbons, Aromatic; D007202:Indicators and Reagents; D009570:Nitriles; C014356:benzonitrile