An Aza-Wittig Route to Isoquinolines from Azidoarylacrylates
- 23 July 2008
- journal article
- synthesis of-heterocycles
- Published by Georg Thieme Verlag KG in Synfacts
- Vol. 2008 (08) , 0811
- https://doi.org/10.1055/s-2008-1077936
Abstract
The reaction of 2-azido-3-arylacrylates with α-diazocarbonyl compounds and triphenylphosphine to furnish isoquinolines in good to excellent yields is reported. This mechanistically interesting process is proposed to involve a Wolff rearrangement, an aza-Wittig reaction and an electrocyclic ring closure. In reaction I, conditions of refluxing xylenes are required; for reaction II, high regioselectivity (>95:5) in favor of compound A was generally observed. Only for R¹ = 4-F, a non-regioselective result (A:B = 50:50) was observed. The substrate scope was well studied.Keywords
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