Facile synthesis of 4H-1,3-benzoselenazines by the aryne reaction

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, addit...

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Bibliographic Details
Published inHeterocycles Vol. 63; no. 5; pp. 1067 - 1075
Main Authors Rao, UN, Sathunuru, R, Biehl, ER
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 01.05.2004
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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Summary: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 I of 3-methoxybenzyne and 3,4-dimethoxybenzyne.
ISSN:0385-5414
1881-0942
DOI:10.3987/com-04-10006