Phosphorylthioacetamides in the synthesis of annulated quinoxalines

被引:1
作者
Aleksanyan, D. V. [1 ]
Kozlov, V. A. [1 ]
Odinets, I. L. [1 ]
Petrovskii, P. V. [1 ]
Mastryukova, T. A. [1 ]
机构
[1] Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 119991, Russia
基金
俄罗斯基础研究基金会;
关键词
phosphorylthioacetamides; 2,3-dichloroquinoxaline; N-methylquinoxalinium iodide; annulation; 1,3,3a,4,9,9a-hexahydro-2H-pyrrolo[2,3-b]quinoxaline-2-thiones;
D O I
10.1007/s11172-007-0157-2
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Diethoxyphosphorylthioacetamide in the reaction with 2,3-dichloroquinoxaline acted as a thionating reagent, giving diethoxyphosphorylacetonitrile and 2-chloro-3-[(3-chloro-2-quinoxalinyl)thio]quinoxaline. Reactions of phosphorylthioacetamides with N-methylquinoxalinium iodide in alcohol media in the presence of a base proceeded stereoselectively to afford cis-3-phosphoryl-1,3,3a,4,9,9a-hexahydro-2H-pyrrolo[2,3-b]quinoxaline-2-thiones.
引用
收藏
页码:1049 / 1052
页数:4
相关论文
共 19 条
[1]  
*AK NAUK ARM SSR, 1972, HET SYNTH
[2]  
BAKLYKOV VG, 1984, CHEM HETEROCYCL COMP, P549
[3]  
CHADHA VK, 1980, J INDIAN CHEM SOC, V57, P946
[4]   REACTIONS OF AZINES WITH BIFUNCTIONAL NUCLEOPHILES - CYCLIZATIONS AND RING TRANSFORMATIONS [J].
CHARUSHIN, VN ;
CHUPAKHIN, ON ;
VANDERPLAS, HC .
ADVANCES IN HETEROCYCLIC CHEMISTRY, 1988, 43 :301-353
[5]  
CHARUSHIN VN, 1985, CHEM HETEROCYCL COMP, P839
[6]  
CHARUSHIN VN, 1985, CHEM HETEROCYCL COMP, P331
[7]  
CHARUSHIN VN, 1983, CHEM HETEROCYCL COMP, P901
[8]  
Chupakhin ON, 2002, USP KHIM+, V71, P803
[9]   Novel N1-(benzyl)cinnamamidine derived NR2B subtype-selective NMDA receptor antagonists [J].
Curtis, NR ;
Diggle, HJ ;
Kulagowski, JJ ;
London, C ;
Grimwood, S ;
Hutson, PH ;
Murray, F ;
Richards, P ;
Macaulay, A ;
Wafford, KA .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (04) :693-696
[10]  
ELSHAFEI AK, 1981, GAZZ CHIM ITAL, V111, P409