Novel borane reduction of ether-protected aromatic lactams.
Borane reduction of ether-protected aromatic lactams produces 1-alkyl-1,2,3,4-tetrahydroquinolines (5 and 6) in excellent yields. This reaction provides a novel one-pot tandem process for reduction of amide group and N-protected groups. Experimental results demonstrate that the reaction proceeds through two consecutive elimination and reductions via two C-O bond cleavages to form the foresaid products.
Hu
Wan-Ping
WP
Faculty of Biotechnology, Kaohsiung Medical University, Kaohsiung City 807, Taiwan.
Tsai
Pei-Ching
PC
Hsu
Ming-Kuan
MK
Wang
Jeh-Jeng
JJ
D001880:Boranes / Q000737:chemistry*; D004987:Ethers / Q000737:chemistry*; D007769:Lactams / Q000737:chemistry*; D015394:Molecular Structure
D001880:Boranes; D004987:Ethers; D007769:Lactams