Electronic effects in the reaction of 1,3-diaryl-1,3-diketones with hydrazinopyridines
The regioselectivity of the condensation of electronically unsymmetrical 1,3-diaryl-1,3-diketones with 2-hydrazinopyridine and 2,6-bis-hydrazinopyridine to form N-(2-pyridyl)-3,5-diarylpyrazoles was studied. Significant electronic effects on regioselectivities were observed, and regioselectivities were opposite to those exhibited by perfluoroalkyl/alkyl 1,3-diketones. The electronic effects correlate well to the difference between the Hammett σ+ coefficients of the para substituents on the aryl rings. © 2008 Elsevier Ltd. All rights reserved.
Duncan, N., Garner, C., Nguyen, T., Hung, F., & Klausmeyer, K. (2008). Electronic effects in the reaction of 1,3-diaryl-1,3-diketones with hydrazinopyridines. Tetrahedron Letters, 49 (40), 5766-5769. https://doi.org/10.1016/j.tetlet.2008.07.104