Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore
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Org. Biomol. Chem., 2013,11, 6003-6007
07 Jul 2013,
24 Jul 2013
First published online
30 Jul 2013
Concise synthesis of 1,2,4-oxadiazoles was achieved by heating N-benzyl amidoximes with K3PO4 in DMF at 60 °C under an O2 atmosphere via benzylic C–H oxygenation. On the other hand, aerobic treatment of N-benzyl amidoximes with Cs2CO3 in DMSO at 100 °C could result in oxidative skeletal rearrangement to deliver quinazolinones as a major product. This orthogonal product selectivity could be realized by difference of the reaction temperature as well as selection of the solvents and inorganic bases.
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Organic & Biomolecular Chemistry
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