Categories: Synthesis of N-Heterocycles > benzo-fused N-Heterocycles >
Synthesis of Quinazolinediones
Recent Literature
A tandem palladium-catalyzed arylation-ester amidation sequence allows the
synthesis of various quinazolinedione products by reaction of o-halo
benzoates with monoalkyl ureas. The reactions are regioselective for the
formation of 3-N-alkyl isomers.
M. C. Willis, R. H. Snell, A. J. Fletcher, R. L. Woodward, Org. Lett., 2006, 8, 5089-5091.
An efficient method for the synthesis of disubstituted quinazoline diones with
differential N-substitution proceeds in high yields under mild conditions. The
reaction tolerates a wide range of substitutions on the aromatic and dione
rings.
E. Durham, D. Perkins, J. S. Scott, J. Wang, S. Watson,
Synlett, 2016, 27, 965-968.
A Pd-catalyzed insertion and cycloaddition of CO2 and isocyanide to
2-iodoanilines provides quinazoline-2,4(1H,3H)-diones under mild
conditions through the formation of C-C, C-O, and C-N bonds.
P. Xu, F. Wang, T.-Q. Wei, L. Yin, S.-Y. Wang, S.-J. Ji, Org. Lett.,
2017, 19, 4484-4487.
A metal-free N-H and C-H carbonylation process using phenyl isocyanate as
carbonyl source provides a range of synthetically valuable quinazoline-2,4(1H,3H)-diones,
2H-benzo[e] [1,2,4] thiadiazin-3(4H)-one 1,1-dioxides, and
pyrrolo[1,2-a] quinoxalin-4(5H)-ones. The protocol features broad
substrates, excellent yields, mild conditions, and good functional group
compatibility.
K. Govindan, A. Jayaram, T. Duraisamy, N.-Q. Chen, W.-Y. Lin, J. Org. Chem., 2022, 87,
8719-8729.
XANTPHOS has been identified as the optimal ligand for a nickel(0)-catalyzed
synthesis of quinazolinediones from isatoic anhydrides and isocyanates.
Preliminary results on an asymmetric synthesis of atropisomeric
quinazolinediones are reported too.
G. L. Beutner, Y. Hsiao, T. Razler, E. M. Simmons, W. Wertjes, Org. Lett.,
2017, 19, 1052-1055.