BF3-Etherate-Promoted Cascade Reaction of 2-Alkynylanilines with Nitriles: One-Pot Assembly of 4-Amido-Cinnolines.
A BF3-etherate-promoted cascade reaction of nitriles with 2-alkynylanilines is described. This method achieves the formation of two new C-N bonds through a reaction sequence of diazotization with t-BuONO, nucleophilic addition of the alkyne to the BF3-coordinated diazonium ion, followed by nitrile addition to the intermediary vinyl cation and hydrolysis. The method provides efficient and general access to a variety of 4-amido-cinnolines. Notable features of the method include its broad functional group tolerance and avoidance of transition metals.
Department of Medicinal and Applied Chemistry and ‡Department of Biotechnology, Kaohsiung Medical University , No. 100, Shih-Chuan First Road, Sanmin District, Kaohsiung City 807, Taiwan.
Gopal Chandru
GC
Senadi
Department of Medicinal and Applied Chemistry and ‡Department of Biotechnology, Kaohsiung Medical University , No. 100, Shih-Chuan First Road, Sanmin District, Kaohsiung City 807, Taiwan.
Babasaheb Sopan
BS
Gore
Department of Medicinal and Applied Chemistry and ‡Department of Biotechnology, Kaohsiung Medical University , No. 100, Shih-Chuan First Road, Sanmin District, Kaohsiung City 807, Taiwan.
Wan-Ping
WP
Hu
Department of Medicinal and Applied Chemistry and ‡Department of Biotechnology, Kaohsiung Medical University , No. 100, Shih-Chuan First Road, Sanmin District, Kaohsiung City 807, Taiwan.
Jeh-Jeng
JJ
Wang