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).
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Additional information
Dedicated to Professor M. A. Yurovskaya on her jubilee.
Latvian Institute of Organic Synthesis, Riga LV-1006, Latvia. email: peteris@osi.lv. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 348–361, March, 2000.
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Suna, E., Trapencieris, P. Synthesis of racemic 1,2,3,4-tetrahydroisoquinolines and their resolution. Chem Heterocycl Compd 36, 287–300 (2000). https://doi.org/10.1007/BF02256866
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DOI: https://doi.org/10.1007/BF02256866