Abstract
1-Hydroxymethylbenzotriazole reacts with phenylethylamines to give the respective N,N-bis(benzotriazol-1-
ylmethyl)phenylethylamines, which are then subject to an intramolecular Friedel–Crafts cyclisation at room
temperature to yield N-benzotriazol-1-ylmethyl-1,2,3,4-tetrahydroisoquinolines. These crystalline UV- and oxygenstable
products can be reduced at room temperature to the corresponding N-methyl-1,2,3,4-tetrahydroisoquinolines
using NaBH4. The method offers an elegant approach to a wide range of N-methylated 1,2,3,4-tetrahydroisoquinolines
since it can be applied not only for the synthesis of 1,2,3,4-tetrahydroisoquinolines with electron-donating
substituents on the aromatic moiety, but also for deactivated derivatives. All steps involved work under very mild
conditions in high to excellent yields.
ylmethyl)phenylethylamines, which are then subject to an intramolecular Friedel–Crafts cyclisation at room
temperature to yield N-benzotriazol-1-ylmethyl-1,2,3,4-tetrahydroisoquinolines. These crystalline UV- and oxygenstable
products can be reduced at room temperature to the corresponding N-methyl-1,2,3,4-tetrahydroisoquinolines
using NaBH4. The method offers an elegant approach to a wide range of N-methylated 1,2,3,4-tetrahydroisoquinolines
since it can be applied not only for the synthesis of 1,2,3,4-tetrahydroisoquinolines with electron-donating
substituents on the aromatic moiety, but also for deactivated derivatives. All steps involved work under very mild
conditions in high to excellent yields.
Original language | English |
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Pages (from-to) | 179-184 |
Number of pages | 6 |
Journal | Journal of the Chemical Society - Perkin Transactions 1 |
Issue number | 2 |
DOIs |
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Publication status | Published - 1999 |