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Synfacts 2008(11): 1143-1143  
DOI: 10.1055/s-0028-1083486
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Halogen Electrophile Induced Cyclization Route to Isoquinoline N-Oxides

Contributor(s): Victor Snieckus, Toni Rantanen
Q. Ding, J. Wu*
Fudan University, Shanghai, Shanghai Institute of Organic Chemistry, and Jiangxi Normal University, Nanchang, P. R. of China
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Publication History

Publication Date:
23 October 2008 (online)

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Significance

The present article describes an electrophilic cyclization between ortho-alkynylbenzaldehyde oximes and various halogen electrophiles to afford 4-halo-isoquinoline N-oxides. The substrate scope was adequately studied and the yields range generally from good to excellent, an exception being the case of R¹ = 4,5-(OCH2O), R² = Ph and electrophile = Br2 (25% yield). The utility of the products was shown in further Pd-catalyzed Suzuki-Miyaura cross-coupling reactions to give 4-aryl products.