REACTIONS OF HYDROXYLAMINES WITH ETHYL CYANOFORMATE - PREPARATION OF AMINONITRONES AND THEIR SYNTHETIC APPLICATIONS

被引:46
作者
BRANCO, PS
PRABHAKAR, S
LOBO, AM
WILLIAMS, DJ
机构
[1] UNIV NOVA LISBOA,DEPT QUIM,SECCAO QUIM ORGAN APLICADA,CAMPUS FCT-UNL,QUINTA TORRE,P-2825 MONTE DE CAPARICA,PORTUGAL
[2] INST NACL INVEST CIENTIF,CTR QUIM ESTRUTURAL,P-1096 LISBON,PORTUGAL
[3] UNIV NOVA LISBOA,SINTOR,P-2825 MONTE DE CAPARICA,PORTUGAL
关键词
ETHYL CYANOFORMATE; HYDROXYLAMINE; ALPHA-AMINONITRONE; NITROGEN HETEROCYCLES;
D O I
10.1016/S0040-4020(01)88224-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of hydroxylamines with ethyl cyanoformate 1 leads to the formation of carbethoxyamino nitrones 2. UV spectroscopy provided information that suggested the nitrone structure for these compounds in solution. X-ray analysis of 2a confirmed that it exists entirely in the nitrone form in the solid state. These nitrones are shown to be excellent starring materials for a variety of nitrogen containg compounds, namely, imidazoles. benzimidazoles, benzimidazolones, oxadiazolones, N-arylamidines and quinoxalone.
引用
收藏
页码:6335 / 6360
页数:26
相关论文
共 44 条
[1]   SUBSTITUTION AT TETRACOORDINATE SULFUR(VI) - REARRANGEMENT OF 2-AMINOARYL ARENESULFONATES TO N-(2-HYDROXYARYL)ARENESULFONAMIDES [J].
ANDERSEN, KK ;
GOWDA, G ;
JEWELL, L ;
MCGRAW, P ;
PHILLIPS, BT .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (10) :1884-1889
[2]   NITROXIDES .4. PREPARATION OF AZOMETHINE NITROXIDES [J].
AURICH, HG .
CHEMISCHE BERICHTE-RECUEIL, 1968, 101 (05) :1761-&
[3]  
BACCHETTI T, 1961, GAZZ CHIM ITAL, V91, P1475
[4]   STRUCTURE OF AMIDOXIMES [J].
BELL, CL ;
NAMBURY, CNV ;
BAUER, L .
JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (10) :2873-&
[5]   SYNTHESIS AND SOME REACTIONS OF N-HYDROXYCARBAMATES [J].
BOYLAND, E ;
NERY, R .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1966, (03) :346-+
[6]   NITRILE SULFIDES .7. SYNTHESIS OF [1]BENZOPYRANO[4,3-C]ISOTHIAZOLES AND ISOTHIAZOLO[4,3-C]QUINOLINES [J].
BROWNSORT, PA ;
PATON, RM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (11) :2339-2344
[7]  
BUNCEL E, 1985, ISR J CHEM, V26, P313
[8]  
BUSCH M, 1911, CHEM BER, V44, P1573
[9]  
CARPENTER AJ, 1983, J CHEM RES-S, P1913
[10]  
CECCHETTI V, 1984, HETEROCYCLES, V22, P2293