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Synthesis of some N-methyl-l,2,3,4-tetrahydroisoquinolines by Friedel-Crafts cyclisation using benzotriazole auxiliary

Locher, Cornelia and Peerzada, Naseem Hasan (1999). Synthesis of some N-methyl-l,2,3,4-tetrahydroisoquinolines by Friedel-Crafts cyclisation using benzotriazole auxiliary. Journal of the Chemical Society - Perkin Transactions 1,(2):179-184.

Document type: Journal Article
Citation counts: Scopus Citation Count Cited 12 times in Scopus Article | Citations

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Title Synthesis of some N-methyl-l,2,3,4-tetrahydroisoquinolines by Friedel-Crafts cyclisation using benzotriazole auxiliary
Author Locher, Cornelia
Peerzada, Naseem Hasan
Journal Name Journal of the Chemical Society - Perkin Transactions 1
Publication Date 1999
Issue Number 2
ISSN 0300-922X   (check CDU catalogue open catalogue search in new window)
Scopus ID 2-s2.0-0000314374
Start Page 179
End Page 184
Total Pages 6
Place of Publication United Kingdom
Publisher Royal Society of Chemistry
Field of Research CHEMICAL SCIENCES
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.
DOI http://dx.doi.org/10.1039/A807543C   (check subscription with CDU E-Gateway service for CDU Staff and Students  check subscription with CDU E-Gateway in new window)
 
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Created: Fri, 29 Aug 2014, 19:55:04 CST by Anthony Hornby