Rearrangement strategy for the synthesis of 2-aminoanilines

Achim Porzelle, Michael D Woodrow, Nicholas C. O. Tomkinson

Research output: Contribution to journalLetter

12 Citations (Scopus)

Abstract

Treatment of N-aryl hydroxylamines with trichloroacetonitrile in the presence of Imidazole provides a simple and effective method for the preparation of synthetically versatile 2-aminoanilines. Reactions proceed in DMF at 40 degrees C, providing the products in up to 86% isolated yield.
Original languageEnglish
Pages (from-to)1492-1495
Number of pages4
JournalOrganic Letters
Volume12
Issue number7
DOIs
Publication statusPublished - 2 Apr 2010

Fingerprint

Hydroxylamines
imidazoles
preparation
synthesis
products
imidazole
trichloroacetonitrile

Keywords

  • privileged structures
  • hydroxylamines
  • chemistry
  • iodides

Cite this

Porzelle, Achim ; Woodrow, Michael D ; Tomkinson, Nicholas C. O. / Rearrangement strategy for the synthesis of 2-aminoanilines. In: Organic Letters. 2010 ; Vol. 12, No. 7. pp. 1492-1495.
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Rearrangement strategy for the synthesis of 2-aminoanilines. / Porzelle, Achim; Woodrow, Michael D; Tomkinson, Nicholas C. O.

In: Organic Letters, Vol. 12, No. 7, 02.04.2010, p. 1492-1495.

Research output: Contribution to journalLetter

TY - JOUR

T1 - Rearrangement strategy for the synthesis of 2-aminoanilines

AU - Porzelle, Achim

AU - Woodrow, Michael D

AU - Tomkinson, Nicholas C. O.

PY - 2010/4/2

Y1 - 2010/4/2

N2 - Treatment of N-aryl hydroxylamines with trichloroacetonitrile in the presence of Imidazole provides a simple and effective method for the preparation of synthetically versatile 2-aminoanilines. Reactions proceed in DMF at 40 degrees C, providing the products in up to 86% isolated yield.

AB - Treatment of N-aryl hydroxylamines with trichloroacetonitrile in the presence of Imidazole provides a simple and effective method for the preparation of synthetically versatile 2-aminoanilines. Reactions proceed in DMF at 40 degrees C, providing the products in up to 86% isolated yield.

KW - privileged structures

KW - hydroxylamines

KW - chemistry

KW - iodides

U2 - 10.1021/ol100196a

DO - 10.1021/ol100196a

M3 - Letter

VL - 12

SP - 1492

EP - 1495

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 7

ER -