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Paper | Regular issue | Vol 63, No. 5, 2004, pp.1067-1075
Published online, 5th March, 2004
DOI: 10.3987/COM-04-10006
Facile Synthesis of 4H-1,3-Benzoselenazines by the Aryne Reaction

U. Narasimha Rao, Ramadas Sathunuru, and Edward R. Biehl*

*Chemistry Department, Southern Methodist University, Dallas, TX 75275-0314, U.S.A.


Attempts to prepare benzoselenazoles by trapping benzynes with selenoureas failed. These reactions gave instead symmetrically substituted diaryl diselenides. However, when the selenoureas were converted to selenoazadienes, 4H-1,3-benzoselenazines were obtained in excellent yields. Furthermore, addition of the selenium atom of the selenoazadienes occurred regioselectively at the position 1 of 3-methoxybenzyne and 3,4-dimethoxybenzyne.