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Cyclocondensation of Arylhydrazines with 1,3-Bis(het)arylmonothio-1,3-diketones and 1,3-Bis(het)aryl-3-(methylthio)-2-propenones: Synthesis of 1-Aryl-3,5-bis(het)arylpyrazoles with Complementary Regioselectivity

S. Vijay Kumar, Santosh K. Yadav, B. Raghava, B. Saraiah, H. Ila*, K. S. Rangappa* and Arpan Hazra

*Jawaharlal Nehru Centre for Advanced Scientific Research, Jakkur, Bangalore-560064, India, Department of Chemistry, Indian Institute of Technology, Kanpur-208016, India, Email: hilajncasr.ac.in, rangappaksyahoo.com

S. V. Kumar, S. K. Yadav, B. Raghava, B. Saraiah, H. Ila, K. S. Ragappa, A. Hazra, J. Org. Chem., 2013, 78, 4960-4973.

DOI: 10.1021/jo400599e (free Supporting Information)



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Abstract

Two highly regioselective routes enable the synthesis of unsymmetrically substituted pyrazoles with complementary regioselectivity from active methylene ketones. The reaction of the easily accessible 1,3-bisaryl-monothio-1,3-diketone or 3-(methylthio)-1,3-bisaryl-2-propenones with arylhydrazines furnished 1-aryl-3,5-bisarylpyrazoles with complementary regioselectivity at position 3 and 5.


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Key Words

Pyrazoles


ID: J42-Y2013