Categories: Synthesis of N-Heterocycles >
Synthesis of 1,2,3-triazines
Recent Literature
Readily accessible (Z)-4-aryl-2,4-diazido-2-alkenoates can efficiently be
converted to 6-aryl-1,2,3-triazine-4-carboxylate esters under mildly basic
conditions without the assistance of any transition metals or strong acid.
H. Sugimura, R. Takeuichi, S. Ichikawa, E. Nagayama, I. Sasaki, Org. Lett.,
2018, 20, 3434-3437.
A concerted SNAr reaction of 5-bromo-1,2,3-triazines provides
5-aryloxy-1,2,3-triazines via a nonclassic mechanism. 5-aryloxy-1,2,3-triazines
could be used as convenient precursors to access biologically important
3-aryloxy-pyridines in one-pot manner.
H. Luo, Y. Li, Y. Zhang, Q. Lu, Q. An, M. Xu, S. Li, J. Li, B. Li, J. Org. Chem., 2022, 87,
2590-2600.
1,2,3-Triazine 1-oxides are formed by addition of tert-butyl nitrite
to the vinylogous position of vinyl diazo compounds. This formal [5 + 1]
cycloaddition occurs under mild conditions with high functional group tolerance
and regioselectivity, and can be employed for late-stage functionalization. Upon
heating in refluxing chlorobenzene, an extrusion of N2 provides
isoxazoles in very high yields.
L. De Angelis, H. Zheng, M. T. Perz, H. Arman, M. P. Doyle, Org. Lett., 2021, 23,
6542-6546.
