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Paper | Regular issue | Vol 55, No. 1, 2001, pp.163-170
Published online, 1st January, 1970
DOI: 10.3987/COM-00-9087
Fluorenyl Participated Ring Transformation of Urazoles to Triazinanediones

Yong Gong,* Mark J. Bausch,* and Linhua Wang

*Department of Medicinal Chemistry, Aventis Pharmaceuticals, Route 202-206, P.O. Box 6800, Bridgewater, NJ 08807, U.S.A.


Fluorenylation of 1,4-disubstituted urazole (1) with 9-bromofluorene affords corresponding fluorenylurazole (2) along with the rearrangement product triazinanedione (3). The ratio of two products is closely related to the acidity of starting urazole (1). Compound (2) can be transformed into 3 upon treated with potassium t-butoxide. A mechanism involving N-acylimine as ring opening intermediate is proposed. The dual roles of urazole anion (l-K) are discussed.