Categories: Synthesis of N-Heterocycles > benzo-fused N-Heterocycles >
Synthesis of 2,3-dihydroquinazolinones
Recent Literature
The use of a readily available Sc(III)-inda-pybox as the catalyst enabled an
enantioselective synthesis of 2,3-dihydroquinazolinones (DHQZs) via a metal
catalyzed asymmetric intramolecular amidation of an imine.
M. Prakash, V. Kesavan, Org. Lett., 2012,
14, 1896-1899.
An L-proline nitrate assisted protocol enables the construction of
2,3-dihydroquinazolin-4(1H)-ones. The catalyst can be recovered and is
reusable.
S. P. Bahekar, N. D. Dahake, P. B. Sarode, H. S. Chandak,
Synlett, 2015, 26, 2575-2577.
Fluorescent carbon dots are an effective and recyclable carbocatalyst for the
synthesis of 2,3-dihydroquinazolinon-4(1H)-one derivatives and
aza-Michael adducts under mild reaction conditions. This nanoscale form of
carbon may serve as an alternative catalyst for important acid catalyzed organic
transformations.
B. Majumdar, S. Mandani, T. Bhattacharya, D. Sarma, T. K. Sarma, J. Org. Chem.,
2017, 82, 2097-2106.
The use of [Ce(l-Pro)2]2 (Oxa) as recyclable heterogeneous
catalyst enables the preparation of 2-aryl-2,3-dihydroquinazolin-4(1H)-one
derivatives from anthranilamide and several aldehydes under mild conditions in
ethanol at 50-55°C. The catalyst can be recycled and reused three times without
significant loss of catalytic activity.
R. Katla, R. Chowrasia, C. D.G. da Silva, A. R. de Oliveira, B. F. dos Santos,
N. L. C. Domingues, Synthesis, 2017,
49, 5143-5148.
Macroporous Amberlyst A26 OH catalyzes a selective hydration of nitriles to
primary amides as well as a base-catalyzed synthesis of 2-substituted 4(1H)-quinazolinones
via reaction of 2-aminobenzonitrile with carbonyl compounds in H2O-EtOH.
F. Tamaddon, F. Pouramini,
Synlett, 2014, 25, 1127-1131.
A transition-metal-free reaction of 2-aminobenzonitriles with aldehydes in
the presence of KOtBu provides dihydroquinazolinones in high yields at
room temperature. The method is also compatible with ketones for the synthesis
of 2,2-disubstituted dihydroquinazolinones.
T. Ghosh, I. Mandal, S. J. Basak, J. Dash, J. Org. Chem., 2021, 86,
14695-14704.
A copper-catalyzed one-pot reaction of 2-nitrobenzonitriles and various carbonyl
compounds in the presence of diboronic acid as a reductant provides
2,3-dihydroquinazolin-4(1H)-ones with good functional-group tolerance in
good yields under mild conditions.
Q. Liu, Y. Sui, Y. Zhang, K. Zhang, Y. Chen, H. Zhou, Synlett, 2020,
31,
275-279.
A cationic Ru-H complex is a highly effective catalyst for a mild deaminative
coupling reaction of 2'-hydroxyaryl ketones with simple amines to form
3-substituted flavanone products. The analogous deaminative coupling reaction of
2-aminobenzamides with branched amines directly formed 3,3-disubstituted
quinazolinone products.
K. Gnyawali, P. T. K. Arachchige, C. S. Yi, Org. Lett., 2022, 24,
218-222.
Copper-catalyzed cascade cyclization reactions between alkenyl boronic esters
and N-H-based nucleophiles enable new approaches for one-pot assembly of
azacycles. Following Chan-Evans-Lam C-N couplings, cyclization processes either
afford dihydroquinazolin-4-ones as hydroamination products or quinolines as
aromatization products in good yields.
Y. Li, Z. Cao, Z. Wang, L. Xu, Y. Wei, Org. Lett.,
2022, 24, 6554-6559.
The reaction between isatoic anhydride, primary amines, and benzylic alcohols in
the presence of HBr in DMSO at 80°C affords 2,3-dihydroquinazolin-4(1H)-ones
in excellent yields via a metal-free oxidative C(sp3)-N coupling
process.
N. R. E. Sheikhi, P. R. Ranjbar,
Synlett, 2018, 29, 912-917.
Self-assembly of phosphatidylcholine in water creates liposomal nanoreactors for
environmentally friendly synthesis of hydroquinazolinones by two- or
three-component reactions, without the use of an extra catalyst or solvent. The
reaction medium can be recycled.
F. Tamaddon, M. KazemiVernamkhasti,
Synlett, 2016, 27, 2510-2514.
Utilizing a recyclable tartaric acid-SDS catalyst system help to achieve a green
synthesis of 2,3-dihydro/spiroquinazolin-4(1H)-ones via three-component
cyclocondensation reaction of isatoic anhydride, amines and aldehydes/ketones.
Mechanochemical activation at room temperature lead to significant improvement
on previously described methods for the synthesis of such compounds even in
large-scale reactions.
R. Sharma, A. K. Pandey, P. M. S. Chauhan, Synlett, 2012, 23,
2209-2214.
