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Synthesis of N-methyl-4-pyridyl-1,2,3,4-tetrahydroisoquinolines via a pictet-spengler cyclisation

✍ Scribed by Laurence Prat; Vincent Levacher; Georges Dupas; Guy Quéguiner; Jean Bourguignon; Ronan Bureau; Cyril Daveu


Book ID
102343295
Publisher
Journal of Heterocyclic Chemistry
Year
2000
Tongue
English
Weight
345 KB
Volume
37
Category
Article
ISSN
0022-152X

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✦ Synopsis


Abstract

The synthesis of N‐methyl‐4‐pyridyl‐1,2,3,4‐tetrahydroisoquinolines (6a,b,c) was achieved via a Pictet‐Spengler cyclization of an activated amino group derivatized in a carbamate form. The obtained compounds have been designed as potential serotonin analogs.


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Pictet-Spengler condensation of N-sulfon
✍ Claudio C. Silveira; Carmem R. Bernardi; Antonio L. Braga; Teodoro S. Kaufman 📂 Article 📅 1999 🏛 Elsevier Science 🌐 French ⚖ 263 KB

The reaction of N-suifonyl-~-phenethylamines with a-chloro-a-phenylseleno acetate/propionate esters under Lewis acid promotion gives moderate to good yields of the corresponding 1,2,3,4-tetrahydroisoquinoline-lcarboxylates. Varying degrees of diastereoselection were obtained using chiral sulfonamide