AlCl3 induced C-N bond formation followed by Pd/C-Cu mediated coupling-cyclization strategy: synthesis of pyrrolo[2,3-b]quinoxalines as anticancer agents

作者：Prasad Bagineni; Kumar K Shiva; Babu P Vijaya; Anusha K; Rambabu D; Kandale Ajit; Vanaja G R; Kalle Arunasree M; Pal Manojit^*

来源：Tetrahedron Letters, 2012, 53(45): 6059-6066.

DOI：10.1016/j.tetlet.2012.08.119

• 2,3-Dichloroquinoxaline
• Pyrrolo[2,3-b]quinoxaline
• AlCl3
• Palladium

AlCl3 facilitated C-N bond forming reaction between 2,3-dichloroquinoxaline and anilines affording a convenient method for the preparation of N-aryl substituted 3-chloroquinoxalin-2-amines. A related N-benzyl derivative, however, was prepared via a conventional method. These N-alkyl/aryl substituted 3-chloroquinoxalin-2-amines on coupling with terminal alkynes in toluene under Pd/C-Cu catalysis afforded a range of 1,2-disubstituted pyrrolo[2,3-b]quinoxalines within 3-5 h in good to excellent yields. Some of the compounds synthesized showed promising anti-proliferative properties when tested in vitro against two cancer cell lines. Docking studies indicated that these molecules interact well with human Akt in silico.

• 出版日期2012-11-7