Categories: Synthesis of N-Heterocycles > benzo-fused N-Heterocycles >
Synthesis of 2,3-dihydroquinolin-4-ones
Recent Literature
A mild and efficient one-pot procedure starting from o-aminoacetophenones
and aromatic aldehydes in the presence of silver(I) triflate provides various
2-aryl-2,3-dihydroquinolin-4(1H)-ones. This method has several advantages,
such as the use of easily available starting materials, the efficiency of the
catalyst, a simple operation, and tolerance of a wide range of functionality in
the aldehydes.
R. P. Pandit, K. Sharma, Y R. Lee,
Synthesis, 2015, 47, 3881-3890.
The use of zirconyl nitrate as a water-tolerant Lewis-acid catalyst enables a
simple, green, and efficient intramolecular cyclization of o-aminochalcones
to provide 2-aryl-2,3-dihydroquinolin-4(1H)-ones under mild reaction
conditions with improved yields.
A. Gorepatil, P. Gorepatil, M. Gaikwad, D. Mhamane, A. Phadkule, V. Ingle,
Synlett, 2018, 29, 235-237.
A convenient environmentally friendly method for the cyclization of
2-aminochalcones to 2-aryl-2,3-dihydroquinolin-4(1H)-ones on the surface
of silica gel impregnated with indium(III) chloride under microwave irradiation
without any solvent has been reported.
K. H. Kumar, D. Muralidharan, P. T. Perumal, Synthesis, 2004,
63-68.
Amino-substituted chalcones undergo a 1,7-hydride shift upon Lewis acid
activation to form a zwitterionic iminium enolate, which collapses to
dihydroquinoline-4-ones in high yields with an excellent diastereoselectivity.
G. Wicker, R. Schoch, J. Paradies, Org. Lett., 2021, 23,
3626-3630.