Regio-controlled synthesis of N-substituted imidazoles

Ning Xi; Shimin Xu; Yuan Cheng; Andrew S. Tasker; Randall W. Hungate; Paul J. Reider

doi:10.1016/j.tetlet.2005.08.138

Regio-controlled synthesis of N-substituted imidazoles

Ning Xi
, Shimin Xu
, Yuan Cheng
, Andrew S. Tasker
, Randall W. Hungate
, Paul J. Reider

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

18 Scopus citations

Abstract

A regio-specific synthesis of N-substituted imidazoles is described. Readily available α-amino acids are converted to α-aminocarbonyl derivatives and reacted with various isothiocyanates to give N-substituted cyclic thioureas. Oxidative or reductive desulfurization of the cyclic thioureas affords structurally diversified imidazoles in good to excellent yields.

Original language	English (US)
Pages (from-to)	7315-7319
Number of pages	5
Journal	Tetrahedron Letters
Volume	46
Issue number	43
DOIs	https://doi.org/10.1016/j.tetlet.2005.08.138
State	Published - Oct 24 2005
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

Keywords

Amino acids
Cyclic thioureas
Imidazoles
Regio-controlled synthesis

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10.1016/j.tetlet.2005.08.138

Cite this

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title = "Regio-controlled synthesis of N-substituted imidazoles",

abstract = "A regio-specific synthesis of N-substituted imidazoles is described. Readily available α-amino acids are converted to α-aminocarbonyl derivatives and reacted with various isothiocyanates to give N-substituted cyclic thioureas. Oxidative or reductive desulfurization of the cyclic thioureas affords structurally diversified imidazoles in good to excellent yields.",

keywords = "Amino acids, Cyclic thioureas, Imidazoles, Regio-controlled synthesis",

author = "Ning Xi and Shimin Xu and Yuan Cheng and Tasker, \{Andrew S.\} and Hungate, \{Randall W.\} and Reider, \{Paul J.\}",

year = "2005",

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doi = "10.1016/j.tetlet.2005.08.138",

language = "English (US)",

volume = "46",

pages = "7315--7319",

journal = "Tetrahedron Letters",

issn = "0040-4039",

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TY - JOUR

T1 - Regio-controlled synthesis of N-substituted imidazoles

AU - Xi, Ning

AU - Xu, Shimin

AU - Cheng, Yuan

AU - Tasker, Andrew S.

AU - Hungate, Randall W.

AU - Reider, Paul J.

PY - 2005/10/24

Y1 - 2005/10/24

N2 - A regio-specific synthesis of N-substituted imidazoles is described. Readily available α-amino acids are converted to α-aminocarbonyl derivatives and reacted with various isothiocyanates to give N-substituted cyclic thioureas. Oxidative or reductive desulfurization of the cyclic thioureas affords structurally diversified imidazoles in good to excellent yields.

AB - A regio-specific synthesis of N-substituted imidazoles is described. Readily available α-amino acids are converted to α-aminocarbonyl derivatives and reacted with various isothiocyanates to give N-substituted cyclic thioureas. Oxidative or reductive desulfurization of the cyclic thioureas affords structurally diversified imidazoles in good to excellent yields.

KW - Amino acids

KW - Cyclic thioureas

KW - Imidazoles

KW - Regio-controlled synthesis

UR - https://www.scopus.com/pages/publications/25444501550

UR - https://www.scopus.com/pages/publications/25444501550#tab=citedBy

U2 - 10.1016/j.tetlet.2005.08.138

DO - 10.1016/j.tetlet.2005.08.138

M3 - Article

AN - SCOPUS:25444501550

SN - 0040-4039

VL - 46

SP - 7315

EP - 7319

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 43

ER -

Regio-controlled synthesis of N-substituted imidazoles

Abstract

All Science Journal Classification (ASJC) codes

Keywords

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