Rearrangement strategy for the synthesis of 2-aminoanilines

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

doi:10.1021/ol100196a

Rearrangement strategy for the synthesis of 2-aminoanilines

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

Pure And Applied Chemistry

Research output: Contribution to journal › Letter › peer-review

19 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 language	English
Pages (from-to)	1492-1495
Number of pages	4
Journal	Organic Letters
Volume	12
Issue number	7
DOIs	https://doi.org/10.1021/ol100196a
Publication status	Published - 2 Apr 2010

Keywords

privileged structures
hydroxylamines
chemistry
iodides

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10.1021/ol100196a

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title = "Rearrangement strategy for the synthesis of 2-aminoanilines",

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.",

keywords = "privileged structures, hydroxylamines, chemistry, iodides",

author = "Achim Porzelle and Woodrow, {Michael D} and Tomkinson, {Nicholas C. O.}",

year = "2010",

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doi = "10.1021/ol100196a",

language = "English",

volume = "12",

pages = "1492--1495",

journal = "Organic Letters",

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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

SN - 1523-7060

VL - 12

SP - 1492

EP - 1495

JO - Organic Letters

JF - Organic Letters

IS - 7

ER -

Rearrangement strategy for the synthesis of 2-aminoanilines

Abstract

Keywords

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