The Boulton-Katritzky reaction represents one of the most popular and efficient strategies used to realize azole-into-azole conversions. For example, under different experimental conditions, it allows the rearrangement of Z-arylhydrazones of 3-benzoyl-5-phenyl-1,2,4-oxadiazoles (1) into 2-aryl-4-benzoylamino-5-phenyl-2H-1,2,3-triazoles (2) in very high yields. Moreover, we have recently realized this conversion also by UV-photostimulation. Now we have enlarged the scope of the reaction irradiating with visible or UV light an acetonitrile solution of some Z-arylhydrazones (1a-e) in the presence of catalytic amounts of Ru(bpY)(2)Cl-2. We have observed the unexpected formation of the 1-aryl-5-benzoylamino-3-phenyl-1,2,4-triazoles (3a-e) eventually together with the expected 2a-d in high yields. (C) 2015 Elsevier Ltd. All rights reserved.
D'Auria, M., Frenna, V., Monari, M., Palumbo-Piccionello, A., Racioppi, R., Spinelli, D., et al. (2015). Ru(bpy)2Cl2: A catalyst able to shift the course of the photorearrangement in the Boulton-Katritzky reaction. TETRAHEDRON LETTERS, 56(47), 6598-6601 [10.1016/j.tetlet.2015.10.030].
Ru(bpy)2Cl2: A catalyst able to shift the course of the photorearrangement in the Boulton-Katritzky reaction
MONARI, MAGDA;SPINELLI, DOMENICO;
2015
Abstract
The Boulton-Katritzky reaction represents one of the most popular and efficient strategies used to realize azole-into-azole conversions. For example, under different experimental conditions, it allows the rearrangement of Z-arylhydrazones of 3-benzoyl-5-phenyl-1,2,4-oxadiazoles (1) into 2-aryl-4-benzoylamino-5-phenyl-2H-1,2,3-triazoles (2) in very high yields. Moreover, we have recently realized this conversion also by UV-photostimulation. Now we have enlarged the scope of the reaction irradiating with visible or UV light an acetonitrile solution of some Z-arylhydrazones (1a-e) in the presence of catalytic amounts of Ru(bpY)(2)Cl-2. We have observed the unexpected formation of the 1-aryl-5-benzoylamino-3-phenyl-1,2,4-triazoles (3a-e) eventually together with the expected 2a-d in high yields. (C) 2015 Elsevier Ltd. All rights reserved.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
