Organic & biomolecular chemistry

Orthogonal aerobic conversion of N-benzyl amidoximes to 1, 2, 4-oxadiazoles or quinazolinones

FL Zhang, YF Wang, S Chiba

文献索引：Zhang, Feng-Lian; Wang, Yi-Feng; Chiba, Shunsuke Organic and Biomolecular Chemistry, 2013 , vol. 11, # 36 p. 6003 - 6007

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被引用次数: 19

摘要

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 ...