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Stirring-controlled mono or double aminocarbonylation of 1,3-bis(2-iodoaryl)propan-2-amines

Author:
Hu, Huaanzi, Xie, Zeqiang, Luo, Shuang, Zhu, Qiang
Source:
Tetrahedron letters 2018 v.59 no.11 pp. 1034-1037
ISSN:
0040-4039
Subject:
chemical reactions, chemical structure, isoquinolines, mixing, palladium, quinolones, tryptamines
Abstract:
A palladium-catalyzed highly selective mono or double aminocarbonylation of 1,3-bis(2-iodoaryl)propan-2-amines under balloon pressure of CO has been developed. Tetracyclic isoquinolino[2,3-b]isoquinolinones were obtained through double aminocarbonylation when the reaction was stirred overnight, as most of organic reactions being operated. We accidentally found that monocarbonylated isoquinolinone products could be formed in good selectivity and chemical yield just without stirring the reaction mixture. The low concentration of CO in the still solution may account for the selectivity.
Agid:
5894838