Various orthodiazonaphthoquinones (1-diazo-2(1H)-naphthalenones and 2-diazo-1(2H)-naphthalenones) were synthesized using the diazo-transfer reaction between the appropriate naphthol and 2-azido-1,3-dimethylimidazolinium chloride (ADMC). The ADMC was prepared by the reaction between 2-chloro-1,3-dimethylimidazolinium chloride and sodium azide. The diazo-transfer reaction selectively introduced the diazo group at the C(2) position of 1-naphthol or the C(1) position of 2-naphthol. The naphthalenediols that were tested, except for 1,3-naphthalenediol, also reacted with ADMC to afford the corresponding monodiazotized compound. X-ray analyses suggested that the diazonaphthoquinones did not have diazoniumnaphtholate structures but had diazocarbonyl structures.
利用1-
萘酚或
2-萘酚与2-
叠氮-1,3-二甲基
咪唑啉氯化物(A
DMC)之间的偶氮转移反应,合成了多种正二偶氮
萘醌类化合物(1-二偶氮-2(1H)-
萘醌和2-二偶氮-1(2H)-
萘醌)。通过2-
氯-1,3-二甲基
咪唑啉氯化物与
叠氮化
钠的反应制备了A
DMC。偶氮转移反应在1-
萘酚的C(2)位或
2-萘酚的C(1)位选择性地引入偶氮基团。除1,3-
萘二
酚外,所测试的
萘二
酚也与A
DMC反应,得到相应的单偶氮化产物。X射线分析表明,这些二偶氮
萘醌结构并非二偶氮
萘酚酸结构,而是二偶氮羰基结构。