General Papers ARKIVOC 2001 (i) 242-268
Recent trends in the chemistry of pyridine N-oxides Shaker Youssif
Department of Chemistry, Faculty of Science, Zagazig University, Zagazig, Egypt
(received 16 Mar 01; accepted 10 Dec 01; published on the web 18 Dec 01)
Abstract
This review describes the synthesis and reactions of pyridine N-oxides within the last ten years. The first part surveys the different synthetic methods which include ring transformation, classical oxidations using peracids, the use of metalloorganic oxidizing agents and cycloaddition reactions. The second part surveys the reactions of pyridine N-oxides including the deoxygenation, nucleophilic reaction and cycloaddition to N-O bond.
Keywords: Synthesis of pyridine N-oxides, reactions of pyridine N-oxides, cycloaddition reactions, metallorganic oxidizing agents
Introduction Spectroscopic properties 1 Synthesis of pyridine N-oxides
1.1 From the esters of N-hydroxy-2-thiopyridone 1.2 By ring transformation of isooxazoles. 1.3. By the oxidation of pyridine derivatives 1.3.1 Using H2O2/ AcOH 1.3.2 Using H2O2/ manganese tetrakis(2,6-dichlorophenyl)porphyrin 1.3.3 Using H2O2/ methyltrioxorhenium (MTO) 1.3.4 Using dimethyldioxirane (DMD) 1.3.5 Using bis(trimethylsilyl)peroxide (BTSP) 1.3.6 Using Caro’s acid 1.3.7 Using m-chloroperoxybenzoic acid 1.3.8 Using oxaziridines 1.4 Through cycloaddition reaction 2 Reactions of pyridine N-oxides
2.1 Deoxygenation 2.2 Rearrangement of allyloxypyridine N-oxide 2.3 Nucleophilic reactions 2.4 Metallation followed by electrophilic substitution ISSN 1424-6376 Page 242 ©ARKAT, USA, Inc
0
