A method for the synthesis of substituted quinolines via electrophilic cyclization of 1-azido-2-(2-propynyl)benzene.
A new and efficient strategy for the synthesis of substituted quinolines via electrophilic cyclization is developed. The intramolecular cyclization of 1-azido-2-(2-propynyl)benzene 1 proceeds smoothly in the presence of electrophilic reagents (I(2), Br(2), ICl, NBS, NIS, and HNTf(2)) in CH(3)NO(2) at room temperature or in the presence of catalytic amounts of AuCl(3)/AgNTf(2) in THF at 100 degrees C to afford the corresponding quinolines 2 in good to high yields. In the case of the electrophilic reagents, E of 2 is either I, Br, or H, depending on the reagent type, while E of 2 is H in the case of the electrophilic catalyst.
Huo
Zhibao
Z
Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan.
Gridnev
Ilya D
ID
Yamamoto
Yoshinori
Y
D001386:Azides / Q000737:chemistry*; D001555:Benzene Derivatives / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D004583:Electrons; D007202:Indicators and Reagents / Q000737:chemistry*; D015394:Molecular Structure; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism
C549278:1-azido-2-(2-propynyl)benzene; D001386:Azides; D001555:Benzene Derivatives; D007202:Indicators and Reagents; D011804:Quinolines; D012997:Solvents