Efficient construction of tri- and tetracyclic heterocycles from linear 1,6-dienes by a domino reaction.
Tri- and tetracyclic heterocycle systems were constructed by a palladium-catalyzed domino reaction of linear 1,6-dienes that contain acryl groups with aryl halides through C-C coupling and aromatic C-H functionalization. Three different acrylamides have been shown to be very active for the reaction. The substituents on the aryl halides could be ethoxycarbonyl, ketyl, chloro, sulfonyl, cyano, etc. Thus, the ready accessibility of the starting materials, the wide range of compatibility of substrates including both dienes and aryl halides, and the generality of this process make the reaction highly valuable in view of the synthetic and medicinal importance of these kinds of heterocycles.
Hu
Yimin
Y
Anhui Key Laboratory of Functional Molecular Solids, Institute of Organic Chemistry, School of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241000, China. yiminhu@mail.ahnu.edu.cn
Song
Fengfa
F
Wu
Fenghua
F
Cheng
Dong
D
Wang
Shaowu
S
D000466:Alkadienes / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism
D000466:Alkadienes; D006571:Heterocyclic Compounds; D010165:Palladium