Synthesis of N-substituted aryl amidines by strong base activation of amines

Muhammad M. Khalifa; Micah J. Bodner; J. Andrew Berglund; Michael M. Haley

doi:10.1016/j.tetlet.2015.05.029

Synthesis of N-substituted aryl amidines by strong base activation of amines

Muhammad M. Khalifa
, Micah J. Bodner
, J. Andrew Berglund
, Michael M. Haley

Biology

University at Albany

University of Oregon

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

21 Scopus citations

Abstract

Abstract We describe an efficient method for the direct preparation of N-substituted aryl amidines from nitriles and primary amines. The protocol employs activation of amines by a strong base and provides greater access to a pharmaceutically relevant functional group. This synthetic approach tolerates deactivated nitriles, nitriles with competing substitution sites, and aryl amines.

Original language	English
Article number	46301
Pages (from-to)	4109-4111
Number of pages	3
Journal	Tetrahedron Letters
Volume	56
Issue number	27
DOIs	https://doi.org/10.1016/j.tetlet.2015.05.029
State	Published - 2015

Keywords

Amidine
Amine
Base-activation
Nitrile
Strong base

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10.1016/j.tetlet.2015.05.029

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title = "Synthesis of N-substituted aryl amidines by strong base activation of amines",

abstract = "Abstract We describe an efficient method for the direct preparation of N-substituted aryl amidines from nitriles and primary amines. The protocol employs activation of amines by a strong base and provides greater access to a pharmaceutically relevant functional group. This synthetic approach tolerates deactivated nitriles, nitriles with competing substitution sites, and aryl amines.",

keywords = "Amidine, Amine, Base-activation, Nitrile, Strong base",

author = "Khalifa, \{Muhammad M.\} and Bodner, \{Micah J.\} and Berglund, \{J. Andrew\} and Haley, \{Michael M.\}",

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year = "2015",

doi = "10.1016/j.tetlet.2015.05.029",

language = "English",

volume = "56",

pages = "4109--4111",

journal = "Tetrahedron Letters",

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T1 - Synthesis of N-substituted aryl amidines by strong base activation of amines

AU - Khalifa, Muhammad M.

AU - Bodner, Micah J.

AU - Berglund, J. Andrew

AU - Haley, Michael M.

PY - 2015

Y1 - 2015

N2 - Abstract We describe an efficient method for the direct preparation of N-substituted aryl amidines from nitriles and primary amines. The protocol employs activation of amines by a strong base and provides greater access to a pharmaceutically relevant functional group. This synthetic approach tolerates deactivated nitriles, nitriles with competing substitution sites, and aryl amines.

AB - Abstract We describe an efficient method for the direct preparation of N-substituted aryl amidines from nitriles and primary amines. The protocol employs activation of amines by a strong base and provides greater access to a pharmaceutically relevant functional group. This synthetic approach tolerates deactivated nitriles, nitriles with competing substitution sites, and aryl amines.

KW - Amidine

KW - Amine

KW - Base-activation

KW - Nitrile

KW - Strong base

UR - https://www.scopus.com/pages/publications/84937420389

U2 - 10.1016/j.tetlet.2015.05.029

DO - 10.1016/j.tetlet.2015.05.029

M3 - Article

SN - 0040-4039

VL - 56

SP - 4109

EP - 4111

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 27

M1 - 46301

ER -

Synthesis of N-substituted aryl amidines by strong base activation of amines

Abstract

Keywords

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