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EFFICIENT AND FACILE ROUTES TO NITRONES

EFFICIENT AND FACILE ROUTES TO NITRONES ORGANIC PREPARATIONS AND PROCEDURES INT., 32 (2), 175-183 (2000) Alan R. Katritzky,*u Xilin Cui," Qiuhe Long, a Baozhen Yanga, Allan L. Wilcoxh and Yong-Kang Zhangh aCenter for Heterocyclic Compoundr, Department of Chemistiy, University of Florida, P. 0. Box 1 17200, Gainesville, FL 3261 1-7200, USA bCen6aur Pharmaceuticals, Inc., 484 Oakmead Parkway, Sunnyvale, CA 94086, USA Azomethine N-oxides, commonly known as nitrones, have been extensively investigated1.2 because of their utility as versatile synthetic intermediates and their relative stability compared with the analogous azomethine imines and azomethine ylides. A nitrone is often viewed as an extended carbonyl group that should be subject to electrophilic attack at the oxygen and nucleophilic attack at the carbon. Nitrones are classic examples of octet-stabilized 1,3-dipoles lacking an orthogonal double bond: As such, they participate in [3+2] cycloaddition reactions with a wide variety of dipolarophiles to provide numerous heterocyclic system^.^^-^* 6a-h Interest in nitrones also stems from their photo- chemical reactivity' as well as from their excellent radical spin-trapping capability leading to their use as antioxidants. * Nitrones are normally synthesized via one of the following routes: i) Condensation of carbonyl compounds with hydroxylamines,' or oxidation of hydroxylaminesl" if the appropriate hydroxylamines are available. ii) Oxidation http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Organic Preparations and Procedures International: The New Journal for Organic Taylor & Francis

EFFICIENT AND FACILE ROUTES TO NITRONES

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Publisher
Taylor & Francis
Copyright
Copyright Taylor & Francis Group, LLC
ISSN
1945-5453
eISSN
0030-4948
DOI
10.1080/00304940009356283
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Abstract

ORGANIC PREPARATIONS AND PROCEDURES INT., 32 (2), 175-183 (2000) Alan R. Katritzky,*u Xilin Cui," Qiuhe Long, a Baozhen Yanga, Allan L. Wilcoxh and Yong-Kang Zhangh aCenter for Heterocyclic Compoundr, Department of Chemistiy, University of Florida, P. 0. Box 1 17200, Gainesville, FL 3261 1-7200, USA bCen6aur Pharmaceuticals, Inc., 484 Oakmead Parkway, Sunnyvale, CA 94086, USA Azomethine N-oxides, commonly known as nitrones, have been extensively investigated1.2 because of their utility as versatile synthetic intermediates and their relative stability compared with the analogous azomethine imines and azomethine ylides. A nitrone is often viewed as an extended carbonyl group that should be subject to electrophilic attack at the oxygen and nucleophilic attack at the carbon. Nitrones are classic examples of octet-stabilized 1,3-dipoles lacking an orthogonal double bond: As such, they participate in [3+2] cycloaddition reactions with a wide variety of dipolarophiles to provide numerous heterocyclic system^.^^-^* 6a-h Interest in nitrones also stems from their photo- chemical reactivity' as well as from their excellent radical spin-trapping capability leading to their use as antioxidants. * Nitrones are normally synthesized via one of the following routes: i) Condensation of carbonyl compounds with hydroxylamines,' or oxidation of hydroxylaminesl" if the appropriate hydroxylamines are available. ii) Oxidation

Journal

Organic Preparations and Procedures International: The New Journal for Organic – Taylor & Francis

Published: Apr 1, 2000

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