Categories: Synthesis of N-Heterocycles >
Synthesis of pyridazines
An unexpected C-C bond cleavage in the absence of metal enables an efficient approach toward 3,6-diarylpyridazines and 6-arylpyridazin-3-ones from simple and commercially available 1,3-dicarbonyl compounds and methyl ketones.
Q. Gao, Y. Zhu, M. Lian, M. Liu, J. Yuan, G. Yin, A. Wu, J. Org. Chem., 2012, 77, 9865-9870.
A copper-promoted 6-endo-trig cyclization of readily available β,γ-unsaturated hydrazones enables an efficient synthesis of a series of 1,6-dihydropyridazines with good yields, high functional group tolerance, and remarkable regioselectivity under mild conditions. Importantly, the 1,6-dihydropyridazines can be efficiently converted to biologically important pyridazines in the presence of NaOH.
Y.-Q. Guo, M.-N. Zhao, Z.-H. Ren, Z.-H. Guan, Org. Lett., 2018, 20, 3337-3340.