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Convenient preparation of some N-substituted 1,2,3,4-tetrahydroisoquinolines lacking electron-donating substituents

Locher, C (2001). Convenient preparation of some N-substituted 1,2,3,4-tetrahydroisoquinolines lacking electron-donating substituents. Synthetic Communications,31(19):2895-2911.

Document type: Journal Article
Citation counts: Scopus Citation Count Cited 2 times in Scopus Article | Citations

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Title Convenient preparation of some N-substituted 1,2,3,4-tetrahydroisoquinolines lacking electron-donating substituents
Author Locher, C
Journal Name Synthetic Communications
Publication Date 2001
Volume Number 31
Issue Number 19
ISSN 0039-7911   (check CDU catalogue open catalogue search in new window)
Scopus ID 2-s2.0-0034853576
Start Page 2895
End Page 2911
Total Pages 17
HERDC Category C1 - Journal Article (DEST)
Abstract N,N-Bis(benzotriazol-1-ylmethyl)-beta -phenylethylamines 3 are cyclised intramolecularly in conc. H2SO4 to the corresponding N-benzotriazol-1-ylmethyl-1,2,3,4-tetrahydroisoquinolines 4. The remaining benzotriazolyl-moiety can be replaced by nucleophiles, leading to N-substituted 1,2,3,4-tetrahydroisoquinolines 5-8.
Keywords bischler-napieralski reaction
pictet-spengler reaction
benzotriazole
mechanism
chemistry
auxiliary
DOI http://dx.doi.org/10.1081/SCC-100105660   (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: Wed, 28 Nov 2007, 14:16:08 CST