Tandem oxidation processes for the preparation of nitrogen-containing heteroaromatic and heterocyclic compounds

S A  Raw; C D  Wilfred; R J K  Taylor

doi:10.1039/b315689c

Tandem oxidation processes for the preparation of nitrogen-containing heteroaromatic and heterocyclic compounds

S A Raw, C D Wilfred, R J K Taylor

Chemistry

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

Abstract

alpha-Hydroxy ketones undergo manganese dioxide-mediated oxidation followed by in situ trapping with aromatic or aliphatic 1,2-diamines to give quinoxalines or dihydropyrazines, respectively, in a one-pot procedure which avoids the need to isolate the highly reactive dicarbonyl intermediates. The scope and limitations of these procedures are outlined and modi. cations to this procedure are discussed in which reduction is carried out in the same reaction vessel, generating piperazines, or oxidation, leading to pyrazines.

Original language	English
Pages (from-to)	788-796
Number of pages	9
Journal	Organic and Biomolecular Chemistry
Volume	2
Issue number	5
DOIs	https://doi.org/10.1039/b315689c
Publication status	Published - 2004

Keywords

ALPHA-AMINO GLYOXALS
MANGANESE-DIOXIDE
BIOLOGICAL-ACTIVITY
WITTIG REACTIONS
QUINOXALINE
REDUCTION
PYRAZINE
POTENT
CONDENSATION
DERIVATIVES

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10.1039/b315689c

Cite this

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title = "Tandem oxidation processes for the preparation of nitrogen-containing heteroaromatic and heterocyclic compounds",

abstract = "alpha-Hydroxy ketones undergo manganese dioxide-mediated oxidation followed by in situ trapping with aromatic or aliphatic 1,2-diamines to give quinoxalines or dihydropyrazines, respectively, in a one-pot procedure which avoids the need to isolate the highly reactive dicarbonyl intermediates. The scope and limitations of these procedures are outlined and modi. cations to this procedure are discussed in which reduction is carried out in the same reaction vessel, generating piperazines, or oxidation, leading to pyrazines.",

keywords = "ALPHA-AMINO GLYOXALS, MANGANESE-DIOXIDE, BIOLOGICAL-ACTIVITY, WITTIG REACTIONS, QUINOXALINE, REDUCTION, PYRAZINE, POTENT, CONDENSATION, DERIVATIVES",

author = "Raw, {S A} and Wilfred, {C D} and Taylor, {R J K}",

year = "2004",

doi = "10.1039/b315689c",

language = "English",

volume = "2",

pages = "788--796",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "The Royal Society of Chemistry",

number = "5",

}

TY - JOUR

T1 - Tandem oxidation processes for the preparation of nitrogen-containing heteroaromatic and heterocyclic compounds

AU - Raw, S A

AU - Wilfred, C D

AU - Taylor, R J K

PY - 2004

Y1 - 2004

N2 - alpha-Hydroxy ketones undergo manganese dioxide-mediated oxidation followed by in situ trapping with aromatic or aliphatic 1,2-diamines to give quinoxalines or dihydropyrazines, respectively, in a one-pot procedure which avoids the need to isolate the highly reactive dicarbonyl intermediates. The scope and limitations of these procedures are outlined and modi. cations to this procedure are discussed in which reduction is carried out in the same reaction vessel, generating piperazines, or oxidation, leading to pyrazines.

AB - alpha-Hydroxy ketones undergo manganese dioxide-mediated oxidation followed by in situ trapping with aromatic or aliphatic 1,2-diamines to give quinoxalines or dihydropyrazines, respectively, in a one-pot procedure which avoids the need to isolate the highly reactive dicarbonyl intermediates. The scope and limitations of these procedures are outlined and modi. cations to this procedure are discussed in which reduction is carried out in the same reaction vessel, generating piperazines, or oxidation, leading to pyrazines.

KW - ALPHA-AMINO GLYOXALS

KW - MANGANESE-DIOXIDE

KW - BIOLOGICAL-ACTIVITY

KW - WITTIG REACTIONS

KW - QUINOXALINE

KW - REDUCTION

KW - PYRAZINE

KW - POTENT

KW - CONDENSATION

KW - DERIVATIVES

U2 - 10.1039/b315689c

DO - 10.1039/b315689c

M3 - Article

SN - 1477-0520

VL - 2

SP - 788

EP - 796

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 5

ER -