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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 35, 2005 - Issue 4
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Original Articles

C‐C Bond Cleavage Studies in Bipyrazoles: A Convenient Synthesis of Pyrazolo‐5‐ols

Shiv P. Singh Department of Chemistry, Kurukshetra University, Kurukshetra, India
,
Rajesh Naithani Department of Chemistry, University of Illinois at Chicago, Chicago, USACorrespondence[email protected]
,
Ranjana Aggarwal Department of Chemistry, Kurukshetra University, Kurukshetra, India
&
Om Prakash Department of Chemistry, Kurukshetra University, Kurukshetra, India
Pages 611-619 | Received 11 Nov 2004, Published online: 12 Apr 2011
 
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Abstract

The treatment of 4‐acetoacetyl derivative (3) of the pyrazoles with hydrazines in ethanol/HCl furnished a variety of bipyrazoles (4). However, when the reaction was performed in sodium acetate/acetic acid/ethanol, different hydrazines gave different products. Under these conditions an unexpected C‐C bond cleavage was observed thus affording a convenient route for the formation of pyrazolo‐5‐ols (5 and 6).

Acknowledgments

The authors are thankful to RSIC, Panjab University, Chandigarh (India) for NMR, IR and elemental analysis data. Financial help from CSIR, New Delhi (India) and Ranbaxy Research Laboratories, New Delhi (India) is gratefully acknowledged.

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