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New Routes to Fused Isoquinolines

✍ Scribed by Enas M. Awad; Nehal M. Elwan; Hamdi M. Hassaneen; Anthony Linden; Heinz Heimgartner

Publisher: John Wiley and Sons
Year: 2002
Tongue: German
Weight: 172 KB
Volume: 85
Category: Article
ISSN: 0018-019X
DOI: 10.1002/1522-2675(200201)85:1<320::aid-hlca320>3.0.co;2-x

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✦ Synopsis

Treatment of 6,7-diethoxy-3,4-dihydroisoquinoline (8) and its 1-methyl derivative 12 with hydrazonoyl halides 10 in the presence of Et 3 N in THF under reflux afforded the corresponding 5,6-dihydro-1,2,4triazolo [3,4-a]isoquinolines 11 and 13, respectively, in high yield (Schemes 2 and 3). The products are formed via regioselective 1,3-dipolar cycloaddition of the intermediate nitrilimines 9 with the isoquinoline CN bond. Reaction of 6,7-diethoxy-3,4-dihydroisoquinoline-1-acetonitrile (4a) with ethyl a-cyanocinnamates 15 in the presence of piperidine in refluxing MeCN yielded benzo[a]quinolizin-4-ones 16 (Scheme 4). Under the same conditions, 12 and arylidene malononitriles 19 reacted to give benzo[a]quinolizin-4-imines 20 (Scheme 5). Instead of 15 and 19, mixtures of an aromatic aldehyde, and ethyl cyanoacetate or malononitrile, respectively, can be used in a one-pot reaction.

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