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Microwave heating of 2-halobenzaldehydes or 2-haloacetophenones with phenylhydrazines at 160°C for 10 min quantitatively yielded the arylhydrazones, which were further cyclized to give 1-aryl-1H-indazoles via CuI/diamine-catalyzed N-arylation under microwave heating (160°C, 10 min). Good to excellent yields were observed for 2-iodo, 2-bromo, and 2-chloro benzaldehydes or acetophenones.
Regina Zibuck,; Mark A. Stahl,; Bobbi Barchiesi,; Peter S. Waalwijk,; Pauline Cohen-Fernandes,; Clarisse L. Habraken. Indazoles studies. 4. Thermolysis of 3-bromo-1-nitro-1H-indazoles in benzene and toluene. Formation of 1-phenyl-1H-indazoles. J. Org. Chem. 1984 , 49(18) ,3310-3314.
Chittari Pabba,; Hong-Jun Wang,; Susan R. Mulligan,; Zhen-Jia Chen,; Todd M. Stark,; Brian T. Gregg. Microwave-assisted synthesis of 1-aryl-1H-indazoles via one-pot two-step Cu-catalyzed intramolecular N-arylation of arylhydrazones. Tetrahedron Letters. 2005, 46 (44), 7553-7557.
Hazard Statements: H315-H319-H335
Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P261-P280a-P305+P351+P338-P304+P340-P405-P501a
Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.