Mild and convenient one pot synthesis of N-hydroxyimides from N-unsubstituted imides

被引:25
作者
Einhorn, C [1 ]
Einhorn, J [1 ]
Marcadal-Abbadi, C [1 ]
机构
[1] Univ Grenoble 1, CNRS, LEDSS UMR 5616, Lab Chim Biomimet, F-38041 Grenoble, France
关键词
D O I
10.1081/SCC-100103264
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new, one pot synthesis of various N-hydroxyimides from N-unsubstituted imides is described. Imides are first transformed into their N-Boc derivatives, which are next reacted with aqueous hydroxylamine, providing crystalline hydroxylammonium salts of the corresponding N-hydroxyimides. Filtration and acidic workup affords pure N-hydroxyimides.
引用
收藏
页码:741 / 748
页数:8
相关论文
共 19 条
[1]   SYNTHESIS OF AN ALPHA-(AMINOOXY)ARYLACETIC ESTER BY THE REACTION OF AN ALPHA-DIAZO ESTER WITH N-HYDROXYPHTHALIMIDE [J].
ACE, KW ;
HUSSAIN, N ;
LATHBURY, DC ;
MORGAN, DO .
TETRAHEDRON LETTERS, 1995, 36 (44) :8141-8144
[2]   USE OF ESTERS OF N-HYDROXYSUCCINIMIDE IN PEPTIDE SYNTHESIS [J].
ANDERSON, GW ;
CALLAHAN, FM ;
ZIMMERMAN, JE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (09) :1839-+
[3]  
AURICH HG, 1989, NITRONES NITRONATES, P318
[4]   A convenient large scale synthesis of O-benzylhydroxylamine [J].
Bonaccorsi, F ;
Giorgi, R .
SYNTHETIC COMMUNICATIONS, 1997, 27 (07) :1143-1147
[5]   SYNTHESIS, BIOLOGICAL EVALUATION, AND QUANTITATIVE STRUCTURE ACTIVITY RELATIONSHIP ANALYSIS OF 2-HYDROXY-1H-ISOINDOLEDIONES AS NEW CYTOSTATIC AGENTS [J].
CHAN, CL ;
LIEN, EJ ;
TOKES, ZA .
JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (03) :509-514
[6]   A new approach for oxygenation using nitric oxide under the influence of N-hydroxyphthalimide [J].
Eikawa, M ;
Sakaguchi, S ;
Ishii, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (13) :4676-4679
[7]   Synthesis of axially chiral N-hydroxyimides, potential new catalysts for asymmetric oxidations [J].
Einhorn, C ;
Einhorn, J ;
Marcadal-Abbadi, C ;
Pierre, JL .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (12) :4542-4546
[8]   Oxidation of organic substrates by molecular oxygen mediated by N-hydroxyphthalimide (NHPI) and acetaldehyde [J].
Einhorn, C ;
Einhorn, J ;
Marcadal, C ;
Pierre, JL .
CHEMICAL COMMUNICATIONS, 1997, (05) :447-448
[9]   Electrocatalytic oxidation of alcohols using substituted N-hydroxyphthalimides as catalysts [J].
Gorgy, K ;
Lepretre, JC ;
Saint-Aman, E ;
Einhorn, C ;
Einhorn, J ;
Marcadal, C ;
Pierre, JL .
ELECTROCHIMICA ACTA, 1998, 44 (2-3) :385-393
[10]   HYDROXAMIC ACIDS AND N-HYDROXYIMIDES RELATED TO PYRIDINE, PYRAZINE, AND QUINOXALINE [J].
HURD, CD ;
BETHUNE, VG .
JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (05) :1471-&