Chemistry of Heterocyclic Compounds

, Volume 36, Issue 3, pp 287–300 | Cite as

Synthesis of racemic 1,2,3,4-tetrahydroisoquinolines and their resolution

  • E. Suna
  • P. Trapencieris
Article

Abstract

1-Aniline-substituted 3,4-dihydroisoquinolines were obtained in various ways using the Bischler-Napieralski reaction. The effect of the protecting group at the aniline nitrogen atom on the course of the reaction has been studied and it was found that the N-phthalyl group was stable under the cyclization conditions. The dihydroisoquinolines were reduced to the racemic 1,2,3,4-tetrahydroisoquinolines which were resolved by crystallization of the diastereomeric tartrates. Two examples of 1,2,3,4-tetrahydroisoquinolines were obtained in optically pure form (>99%ee).

Keywords

dihydroisoquinolines 1,2,3,4-isoquinolines resolution of isomeric tartrates 

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Copyright information

© Kluwer Academic/Plenum Publishers 2000

Authors and Affiliations

  • E. Suna
  • P. Trapencieris

There are no affiliations available

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