Uncatalyzed conversion of linear α-nitro ketones into amides by reaction with primary amines under solventless conditions

被引:29
作者
Ballini, R [1 ]
Bosica, G [1 ]
Fiorini, D [1 ]
机构
[1] Univ Camerino, Dipartimento Sci Chim, I-62032 Camerino, MC, Italy
关键词
nitro ketones; amides; carbon-carbon bond; cleavage; solventless;
D O I
10.1016/S0040-4020(03)00022-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of linear alpha-nitro ketones with primary amines allows the formation of amides through the cleavage of the carbon-carbon bond between the carbonyl group and the carbon-nitro group moiety, promoted by the nucleophilic effect of the amine. The reaction is performed at room temperature, without any catalyst and/or solvent. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1143 / 1145
页数:3
相关论文
共 28 条
[1]   MOLECULAR-REARRANGEMENTS .14. PHOTOLYSIS AND THERMOLYSIS OF PHENYLPROPIONANILIDES [J].
BADR, MZA ;
ALY, MM ;
ABDELLATIF, FF .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (18) :3244-3247
[2]   A NOVEL REACTIVITY OF ALPHA-NITRO KETONE TOSYLHYDRAZONES WITH DBU - SYNTHESIS OF ALPHA,BETA-UNSATURATED ENONE TOSYLHYDRAZONES [J].
BALLINI, R ;
GIANTOMASSI, G .
TETRAHEDRON, 1995, 51 (14) :4173-4182
[3]   A NOVEL, CHEMOSELECTIVE, ONE-POT PROCEDURE FOR THE SIMULTANEOUS DENITRATION DEOXYGENATION OF 2-NITROKETONES BY TSNHNH2-NABH4 [J].
BALLINI, R ;
CASTAGNANI, R ;
MARCANTONI, E .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (23) :3161-3162
[4]  
BALLINI R, 1992, SYNLETT, P64
[5]   A TANDEM DENITRATION DEOXYGENATION OF ALPHA-NITRO KETONES VIA (PARA-TOLYLSULFONYL)HYDRAZONES WITH LITHIUM ALUMINUM-HYDRIDE - A PRACTICAL SYNTHESIS OF (Z)-9-TRICOSENE, THE SEX-PHEROMONE OF THE HOUSEFLY (MUSCA-DOMESTICA) [J].
BALLINI, R ;
PETRINI, M ;
ROSINI, G .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (17) :5159-5161
[6]   NEW AND CONVENIENT SYNTHESIS OF (Z)-HENEICOS-6-EN-11-ONE, THE DOUGLAS-FIR TUSSOCK MOTH (ORGYIA-PSEUDOTSUGATA) SEX-PHEROMONE, AND (Z)-NON-6-EN-2-ONE, THE IMMEDIATE PRECURSOR FOR THE SYNTHESIS OF BREVICOMIN, THE SEX ATTRACTANT OF THE WESTERN PINE-BEETLE DENTROCTONUS-BREVICOMIS [J].
BALLINI, R .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (06) :1419-1421
[7]  
Ballini R, 1999, SYNLETT, P1009
[8]   A NEW STEREOSELECTIVE SYNTHESIS OF (E)-ALPHA,BETA-UNSATURATED-GAMMA-DICARBONYL COMPOUNDS BY THE HENRY REACTION [J].
BALLINI, R ;
BOSICA, G .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (18) :5466-5467
[9]   A NEW, HIGHLY EFFICIENT SYNTHESIS OF CONJUGATED NITROCYCLOALKENES [J].
BALLINI, R ;
PALESTINI, C .
TETRAHEDRON LETTERS, 1994, 35 (31) :5731-5734
[10]   Amberlyst A-21 an excellent heterogeneous catalyst for the conversion of carbonyl compounds to oximes [J].
Ballini, R ;
Barboni, L ;
Filippone, P .
CHEMISTRY LETTERS, 1997, (05) :475-476