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Paper | Special issue | Vol 86, No. 1, 2012, pp.189-201
Published online, 8th May, 2012
DOI: 10.3987/COM-12-S(N)1
A Diversified Approach to the Synthesis of Highly Functionalized Novel Azines and Azoles from 2H-Pyran-2-ones

Pushyamitra Mishra, Sandeep Kumar, Hardesh K. Maurya, Sanjay K. Gautam, Brijesh Kumar, Vishnu K. Tandon,* and Vishnu Ji Ram*

*Department of Chemistry, University of Lucknow, Lucknow, U.P. 226007, India

Abstract

One-pot regioselective synthesis of 2,6-diarylpyrimidines (4), 2,6-disubstituted pyridines (5 and 6), 5-aryl-3-cyanomethyl-1H-pyrazoles (7) through base catalyzed ring transformation of suitably functionalized 2H-pyran-2-ones by arylamidines, cyanamide, ammonium carbonate, hydrazines respectively has been developed. Our synthetic approach opened a new avenue for the regioselective synthesis of 2,6-diarylpyrimidines and 2,6-disubstituted pyridines and cyanomethylpyrazoles. The procedure is very simple, efficient and economically viable. The protocol provides an efficient methodology for the preparation of new class of medicinally useful and highly functionalized azines and azoles from single precursor 2H-pyran-2-ones.