Remote protection prevents unwanted cyclizations with 2-aminopyridines

Graham R. Lawton, Haitao Ji, Richard B. Silverman*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

Abstract

The pyridine nitrogen of the 2-aminopyridine group is sufficiently nucleophilic to undergo intramolecular cyclizations, thereby preventing competing Mitsunobu and other substitution reactions from proceeding at a remote site. Double protection of the 2-amino group effectively blocked reaction at the pyridine nitrogen. This is a rare example of the use of a remote protecting group to block another group from reacting.

Original languageEnglish (US)
Pages (from-to)6113-6115
Number of pages3
JournalTetrahedron Letters
Volume47
Issue number34
DOIs
StatePublished - Aug 21 2006

Keywords

  • 2-Aminopyridines
  • Mitsunobu reaction
  • Prevent cyclization
  • Remote protection
  • Side reaction

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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