2-(2-aminophenyl)-acetaldehyde dimethyl acetal: A novel reagent for the protection of carboxylic acids

Eri Arai, Hidetoshi Tokuyama, Martin S. Linsell, Tohru Fukuyama

Research output: Contribution to journalArticlepeer-review

39 Citations (Scopus)

Abstract

The synthesis and use of 2-(2-aminophenyl)-acetaldehyde dimethyl acetal 1 are described. The amides 2, derived from this amine and carboxylic acids, are stable under basic conditions and thus can be regarded as the protected carboxylic acids. The corresponding carboxylic acids are regenerated by conversion of 2 into indolylamides 3 by treatment with CSA and subsequent hydrolysis with LiOOH or NaOH. In addition, 3 can be easily converted to esters, amides, and aldehydes.

Original languageEnglish
Pages (from-to)71-74
Number of pages4
JournalTetrahedron Letters
Volume39
Issue number1-2
DOIs
Publication statusPublished - 1998 Jan 1
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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