Synthesis of 5-substituted indole derivatives. Part 4: Naratriptan from α-anilinoacetaldehyde dimethylacetal by TiCl4-mediated cyclisation

Béla Pete, Gyula Simig, László Poszávácz, László Töke

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

N-Methyl-3-(1-methyl-4-piperidinyl)-1H-indole-5-ethanesulfonamide (Naratriptan, 2) was prepared from N-methyl-N-phenylmethyl-2-(4-aminophenyl)-ethanesulfonamide (3b) through reductive alkylation with dimethoxyacetaldehyde followed by N-acylation and TiCl4-mediated indolisation, according to Sundberg procedure. The isopropyl group proved to be a useful protecting group for sulfonate esters in a number of transformations but was cleaved in the presence of TiCl4.

Original languageEnglish
Pages (from-to)2441-2455
Number of pages15
JournalHeterocycles
Volume60
Issue number11
DOIs
Publication statusPublished - Nov 1 2003

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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