Azaanthraquinone assembly from N-propargylamino quinone via iodine-induced 6-endo-dig electrophilic cyclization.
An efficient methodology taking advantage of the excellent nucleophilicity of aminoquinone to assemble the azaanthraquinone framework was developed via an iodine-induced 6-endo-dig electrophilic cyclization. Therefore, starting from N-propargylaminoquinones, various 3-iodo-1-azaanthraquinones were obtained in yields ranging from 45% to 90%. The metal-free protocol features facile installation of an iodine atom on the azaanthraquinone ring and benign functional group compatibility.
Fei
Na
N
School of Chemistry and Chemical Engineering, State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing 210093, PR China.
Hou
Qiwen
Q
Wang
Shaozhong
S
Wang
Huaqin
H
Yao
Zhu-Jun
ZJ
D000480:Alkynes / Q000737:chemistry*; D000880:Anthraquinones / Q000138:chemical synthesis* / Q000737:chemistry; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D007455:Iodine / Q000737:chemistry*; D015394:Molecular Structure; D009285:Naphthoquinones / Q000737:chemistry*; D013237:Stereoisomerism
D000480:Alkynes; D000880:Anthraquinones; D001372:Aza Compounds; D009285:Naphthoquinones; D007455:Iodine