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Paper | Special issue | Vol 79, No. 1, 2009, pp.669-680
Published online, 21st November, 2008
DOI: 10.3987/COM-08-S(D)34
Iodobenzene Diacetate–Promoted N–N and N–O Bond Formation for Pyrazolo- and Isoxazolopyrimidine Syntheses

Yasunari Monguchi, Kazuyuki Hattori, Tomohiro Maegawa, Kosaku Hirota, and Hironao Sajiki*

*Laboratory of Medicinal Chemistry, Gifu Pharmaceutical University, 6-1 Mitahora-higashi 5-chome, Gifu 502-8585, Japan

Abstract

Pyrazolo[3,4-d]pyrimidine-4,6-dione derivatives were efficiently synthesized via the intramolecular N–N bond coupling of 5-iminomethyl-6-aminouracil derivatives using iodobenzene diacetate. The oxidative coupling was also applied to the analogous N–O bond formation producing isoxazolo[3,4-d]primidine-4,6-dione derivatives.