Palladium-Catalyzed Synthesis of 5-Iminopyrrolones through Isocyanide Double Insertion Reaction with Terminal Alkynes and Water.
With the combination of Pd(dppf)Cl2and Cu(OAc)2, a variety of 5-iminopyrrolones were synthesized in moderate to good yields from terminal alkynes, isocyanide, and water via isocyanide double insertion and cycloaddition reaction. A plausible reaction mechanism for this process is depicted. Furthermore, selected compounds 3c, 3e, and 3h exhibited good activities against HepG2 (human liver cancer), NCI-H460 (human lung cancer), and SK-OV-3 (human ovarian cancer) cell lines with IC50values in the range of 10.63-22.63 μmol L-1.
State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences of Guangxi Normal University , Guilin 541004, People's Republic of China.
Yan
Y
He
College of Chemistry and Chemical Engineering, Jishou University , Jishou 416000, People's Republic of China.
Ying-Chun
YC
Wang
State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences of Guangxi Normal University , Guilin 541004, People's Republic of China.
Kun
K
Hu
State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences of Guangxi Normal University , Guilin 541004, People's Republic of China.
Xiao-Ling
XL
Xu
State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences of Guangxi Normal University , Guilin 541004, People's Republic of China.
Heng-Shan
HS
Wang
State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences of Guangxi Normal University , Guilin 541004, People's Republic of China.
Ying-Ming
YM
Pan