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Potassium tert-Butoxide Promoted Intramolecular Amination of 1-Aryl-2- (2-nitrobenzylidene)hydrazines: Efficient Synthesis of 1-Aryl-1H-indazoles

Fatemeh Esmaeili-Marandi, Mina Saeedi, Mohammad Mahdavi, Issa Yavari, Alireza Foroumadi, Abbas Shafiee*

*Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, Iran, Email: shafieeatums.ac.ir

F. Esmaeili-Marandi, M. Saeedi, M. Mahdavi, I. Yavari, A. Foroumadi, A. Shafiee, Synlett, 2014, 25, 2605-2608.

DOI: 10.1055/s-0034-1379084 (free Supporting Information)


Abstract

1-Aryl-2-(2-nitrobenzylidene)hydrazines readily undergo intramolecular amination to afford 1-aryl-1H-indazole derivatives in good yields in the presence of potassium tert-butoxide in N,N-dimethylformamide at 100 C. Displacement of the nitro group was achieved in the absence of significant electron-withdrawing substituents.

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Key Words

potassium tert-butoxide, Indazoles, hydrazines, amination, nitro displacement


ID: J60-Y2014