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Synthesis of substituted tetrahydroisoquinolines and benzo[d]azepines from phthalan or isochroman and N-silylaldimines

✍ Scribed by F. Foubelo; C. Gómez; A. Gutiérrez; M. Yus

Publisher
Journal of Heterocyclic Chemistry
Year
2000
Tongue
English
Weight
309 KB
Volume
37
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

The 4,4′‐di‐tert‐butylbiphenyl‐catalyzed lithiation of phthalan (1a) and isochroman (1b) in THF at 0°C affords the corresponding functionalized benzyllithiums 2, which by reaction with N‐silylaldimines yield, after acid‐base work‐up, the expected amino alcohols 3. Successive treatment of these amino alcohols with thionyl chloride and sodium hydroxide yields the corresponding substituted benzofused six‐ and seven‐membered nitrogen‐containing heterocycles 4.

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