Tandem electrophilic cyclization-[3+2] cycloaddition-rearrangement reactions of 2-alkynylbenzaldoxime, DMAD, and Br2.
Tandem electrophilic cyclization-[3+2] cycloaddition-rearrangement reactions of 2-alkynylbenzaldoximes, DMAD, and bromine are described, which afford the unexpected isoquinoline-based azomethine ylides in good to excellent yields. The products could be further elaborated via palladium-catalyzed cross-coupling reactions to generate highly functionalized isoquinoline-based stable azomethine ylides.
Ding
Qiuping
Q
Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, China.
Wang
Zhiyong
Z
Wu
Jie
J
D000480:Alkynes / Q000737:chemistry*; D001966:Bromine / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D007546:Isoquinolines / Q000737:chemistry; D010091:Oximes / Q000737:chemistry*; D028561:Transition Elements / Q000737:chemistry
D000480:Alkynes; D007546:Isoquinolines; D010091:Oximes; D028561:Transition Elements; C022918:acetylenedicarboxylic acid dimethyl ester; C039109:isoquinoline; D001966:Bromine