TY - JOUR
T1 - A method for the synthesis of substituted quinolines via electrophilic cyclization of 1-azido-2-(2-propynyl)benzene
AU - Huo, Zhibao
AU - Gridnev, Ilya D.
AU - Yamamoto, Yoshinori
N1 - Funding Information:
This research was supported by DARPA and ARO under contract DAAG29-85-C-0028. The authors would like to thank Barry Cole for antireflection coating the samples, Robert Horning and Mary Hibbs-Brenner for the X-Ray measurements, Cynthia Kelley and Hai Ly for sample preparation and Tom Nohava for MBE growth.
PY - 2010/2/19
Y1 - 2010/2/19
N2 - (Chemical Equation Presented) 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 (I2, Br 2 , ICl, NBS, NIS, and HNTf2) in CH3NO 2 at room temperature or in the presence of catalytic amounts of AuCl3/AgNTf2 in THF at 100 °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, orH, depending on the reagent type, while E of 2 is H in the case of the electrophilic catalyst.
AB - (Chemical Equation Presented) 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 (I2, Br 2 , ICl, NBS, NIS, and HNTf2) in CH3NO 2 at room temperature or in the presence of catalytic amounts of AuCl3/AgNTf2 in THF at 100 °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, orH, depending on the reagent type, while E of 2 is H in the case of the electrophilic catalyst.
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U2 - 10.1021/jo902603v
DO - 10.1021/jo902603v
M3 - Article
C2 - 20099928
AN - SCOPUS:77249159351
SN - 0022-3263
VL - 75
SP - 1266
EP - 1270
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 4
ER -