New Synthesis and Reactions of Ethyl 5‐amino‐4‐cyano‐1‐phenyl‐1H‐pyrazole‐3‐carboxylate |
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| Authors: | Sachin A. Gangurde Shrikant B. Kanawade Prashant S. Nikam Dinesh C. Bhavsar Raghunath B. Toche |
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| Affiliation: | Organic Chemistry Research Center, Department of Chemistry, K.R.T. Arts, B.H. Commerce and A. M. Science College, University of Pune, Nashik, Maharashtra, India |
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| Abstract: | Synthesis of ethyl 5‐amino‐4‐cyano‐1‐phenyl‐1H‐pyrazole‐3‐carboxylate 5 has been achieved via abnormal Beckmann rearrangement of o‐chloroaldehyde 1 . Reaction of o‐aminocarbonitrile 5 with concentrated H2SO4 furnished expected o‐aminocarboxamide pyrazole 6 . Key intermediates o‐aminocarbonitrile 5 and o‐aminocarboxamide 6 were successfully utilized for the synthesis of pyrazolopyrimidine derivatives. The replacement of Cl in o‐chlorocarbonitrile 3 with secondary amine furnished new synthon 13 , which was further used for the synthesis of polysubstituted heterocycles. The obtained new products were well characterized by IR, 1H and 13C NMR, and mass spectra. |
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