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Synfacts 2008(8): 0811-0811  
DOI: 10.1055/s-2008-1077936
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

An Aza-Wittig Route to Isoquinolines from Azidoarylacrylates

Contributor(s): Victor Snieckus, Toni Rantanen
Y.-Y. Yang, W.-G. Zhou, Z.-B. Chen, D. Hong, Y.-G. Wang*
Zhejiang University, Hangzhou, P. R. of China
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Publication History

Publication Date:
23 July 2008 (online)

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Significance

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.