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One-Pot, Three-Component Approach to the Synthesis of 3,4,5-Trisubstituted Pyrazoles

Ahmed Kamal*, K. N. Visweswara Sastry, D. Chandrasekhar, Geeta Sai Mani, Praveen Reddy Adiyala, Jagadeesh Babu Nanubolu, Kiran Kumar Singarapu and Ram Awatar Maurya*

*CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India, Email: ramauryaiict.res.in, ahmedkamaliict.res.in

A. Kamal, K. N. V. Sastry, D. Chandrasekhar, G. S. Mani, P. R. Adiyala, J. B. Nanubolu, K.  J. Singarapu, R. A. Maurya, J. Org. Chem., 2015, 80, 4325-4335.

DOI: 10.1021/jo502946g (free Supporting Information)


 
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Abstract

A one-pot, three-component coupling of aldehydes, 1,3-dicarbonyls, and diazo compounds as well as tosyl hydrazones enables an operationally simple and high yielding synthesis of polyfunctional pyrazoles. The reaction proceeds through a tandem Knoevenagel condensation, 1,3-dipolar cycloaddition, and transition metal-free oxidative aromatization reaction sequence utilizing molecular oxygen as a green oxidant.

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Key Words

pyrazoles, oxygen


ID: J42-Y2015