Categories: Synthesis of N-Heterocycles, Synthesis of O-Heterocycles > benzo-fused N-Heterocycles, benzo-fused O-Heterocycles >
Synthesis of Benzoxazinones
Recent Literature
Solvent-assisted grinding enables a mild and convenient synthesis of
2-substituted 4H-3,1-benzoxazin-4-ones, 2-aminobenzoxazin-4-ones, and
2-amino-4H-3,1-benzothiazin-4-ones from N-substituted anthranilic
acid derivatives in the presence of 2,4,6-trichloro-1,3,5-triazine and catalytic
triphenylphosphine via a rapid cyclodehydration.
M. Pattarawarapan, S. Wet-osot, D. Yamano, W. Phakhodee,
Synlett, 2017, 28, 589-592.
A facile and efficient copper-catalyzed method for the synthesis of 4H-3,1-benzoxazin-4-one
derivatives is based on a tandem intramolecular C-N coupling/rearrangement
process. This method provides a new and useful strategy for construction of N-heterocycles.
Z.-Y. Ge, Q.-M. Xu, X.-D. Fei, T. Tang, Y.-M. Zhu, S.-J. Ji, J. Org. Chem., 2013,
78, 4524-4529.
A series of substituted benzoxazinones were synthesized from N-(o-bromoaryl)amides
by palladium-catalyzed carbonylation with paraformaldehyde as the carbonyl
source, which is inexpensive, stable, and easy to use.
W. Li, X.-F. Wu, J. Org. Chem.,
2014,
79, 10410-10416.
A highly efficient and practical heterogeneous palladium-catalyzed carbonylative
coupling of 2-iodoanilines with aryl iodides offers a general and powerful tool
for the construction of various valuable 2-arylbenzoxazinones with excellent
atom-economy, high functional group tolerance, good yields, and easy
recyclability of the palladium catalyst.
Z. Xu, B. Huang, Z. Zhou, M. Cai, Synthesis, 2020, 52,
581-590.
A palladium-catalyzed carbonylation of 1-azido-2-iodobenzenes in the presence
of amines provides a broad range of 2-aminobenzoxazinone derivatives in good
yields. By using organic azides as the substrates, external oxidant usage can be
successfully avoided and only N2 is formed as byproduct.
Y. Zhang, Z. Yin, H. Wang, X.-F. Wu,
Org. Lett., 2019, 21, 3242-3246.