A straightforward synthesis of 1,3-dichloro-5,8-dihydroisoquinoline by consecutive Stille cross-coupling and metathesis reactions

Commercially available 2,6-dichloro-4-iodopyridine is converted into 1,3-dichloro-5,8-dihydroisoquinoline via a novel three-step synthesis. An efficient three-step synthetic route from 2,6-dichloro-4-iodopyridine to 1,3-dichloro-5,8-dihydroisoquinoline is described. A ring-closing-metathesis reactio...

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Bibliographic Details
Published in:Tetrahedron letters 2009-09, Vol.50 (35), p.5040-5043
Main Authors: van den Hoogenband, Adri, den Hartog, Jack A.J., Faber-Hilhorst, Nancy, Lange, Jos H.M., Terpstra, Jan Willem
Format: Article
Language:English
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Summary:Commercially available 2,6-dichloro-4-iodopyridine is converted into 1,3-dichloro-5,8-dihydroisoquinoline via a novel three-step synthesis. An efficient three-step synthetic route from 2,6-dichloro-4-iodopyridine to 1,3-dichloro-5,8-dihydroisoquinoline is described. A ring-closing-metathesis reaction constitutes the key step in this synthetic sequence. The reactivity of both chloro atoms is demonstrated in a Suzuki arylation reaction.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2009.06.101