TY - JOUR
T1 - Synthesis of 2-Substituted Quinolines from 2-Aminostyryl Ketones Using Iodide as a Catalyst
AU - Lee, So Young
AU - Jeon, Jiye
AU - Cheon, Cheol-Hong
N1 - Funding Information:
This work was supported by National Research Foundation of Korea (NRF) grants funded by the Korean Government (NRF-2015R1D1A1A01057200 NRF-2017M2A8A4018045, and NRF-20100020209). C.-H.C. appreciates the financial support from an NRF grant funded by the Korean Government (NRF-2014-011165, Center for New Directions in Organic Synthesis).
Publisher Copyright:
© 2018 American Chemical Society.
PY - 2018/5/4
Y1 - 2018/5/4
N2 - A new protocol for the synthesis of 2-substituted quinolines from 2-aminostyryl ketones has been developed using iodide as a nucleophilic catalyst. Conjugate addition of iodide to 2-aminostyryl ketones yielded the corresponding β-iodoketones, which could have a conformation where the amino and carbonyl groups are proximal through free rotation about the Cα-Cβ single bond. Subsequent condensation between the amino and carbonyl groups followed by elimination of hydrogen iodide provided the corresponding quinolines, with regeneration of the iodide catalyst.
AB - A new protocol for the synthesis of 2-substituted quinolines from 2-aminostyryl ketones has been developed using iodide as a nucleophilic catalyst. Conjugate addition of iodide to 2-aminostyryl ketones yielded the corresponding β-iodoketones, which could have a conformation where the amino and carbonyl groups are proximal through free rotation about the Cα-Cβ single bond. Subsequent condensation between the amino and carbonyl groups followed by elimination of hydrogen iodide provided the corresponding quinolines, with regeneration of the iodide catalyst.
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U2 - 10.1021/acs.joc.8b00552
DO - 10.1021/acs.joc.8b00552
M3 - Article
C2 - 29663808
AN - SCOPUS:85046548966
SN - 0022-3263
VL - 83
SP - 5177
EP - 5186
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 9
ER -