A ceric ammonium nitrate N-dearylation of Np-anisylazoles applied to pyrazole, triazole, tetrazole, and pentazole rings: release of parent azoles. Generation of …

RN Butler, JM Hanniffy, JC Stephens…

Index: Butler, Richard N.; Hanniffy, John M.; Stephens, John C.; Burke, Luke A. Journal of Organic Chemistry, 2008 , vol. 73, # 4 p. 1354 - 1364

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Citation Number: 67

Abstract

The reaction of cerium (IV) ammonium nitrate (CAN) with a range of N-(p-anisyl) azoles in acetonitrile or methanol solvents leads to N-dearylation releasing the parent NH-azole and p- benzoquinone in comparable yields. The scope and limitations of the reaction are explored. It was successful with 1-(p-anisyl) pyrazoles, 2-(p-anisyl)-1, 2, 3-triazoles, 2-(p-anisyl)-2 H- tetrazoles, and 1-(p-anisyl) pentazole. The dearylation renders the p-anisyl group as a ...