TY - JOUR
T1 - Gold-Catalyzed Synthesis of (Dihydro)quinolones by Cyclization of Benzaldehyde-Tethered Ynamides and Anilines
AU - Han, Zhengyu
AU - Huang, Jiaxin
AU - Shang, Peinan
AU - Zhu, Xiaolin
AU - Huang, Hai
AU - Sun, Jianwei
N1 - Publisher Copyright:
© 2025 American Chemical Society.
PY - 2025/3/21
Y1 - 2025/3/21
N2 - 2-Quinolones represent a versatile class of compounds that are prevalent in natural and medicinally relevant molecules. Here we report a new approach to the selective formation of these structures. By gold catalysis, a range of benzaldehyde-tethered ynamides reacted with anilines, leading to 4-amino-3,4-dihydro-2-quinolones with high efficiency and excellent diastereoselectivity in dichloromethane. Interestingly, with methyl acetate as the solvent, the same reaction produced 3-aryl 2-quinolones as the major products. The use of a substoichiometric amount of the aniline could also promote this transformation.
AB - 2-Quinolones represent a versatile class of compounds that are prevalent in natural and medicinally relevant molecules. Here we report a new approach to the selective formation of these structures. By gold catalysis, a range of benzaldehyde-tethered ynamides reacted with anilines, leading to 4-amino-3,4-dihydro-2-quinolones with high efficiency and excellent diastereoselectivity in dichloromethane. Interestingly, with methyl acetate as the solvent, the same reaction produced 3-aryl 2-quinolones as the major products. The use of a substoichiometric amount of the aniline could also promote this transformation.
UR - https://www.webofscience.com/wos/woscc/full-record/WOS:001443363100001
UR - https://openalex.org/W4408356967
UR - https://www.scopus.com/pages/publications/105001068728
U2 - 10.1021/acs.orglett.5c00752
DO - 10.1021/acs.orglett.5c00752
M3 - Journal Article
C2 - 40073294
SN - 1523-7060
VL - 27
SP - 2799
EP - 2805
JO - Organic Letters
JF - Organic Letters
IS - 11
ER -