Synthesis and Single Crystal Structures of Substituted-1,3-Selenazol-2-amines

被引:6
作者
Hua, Guoxiong [1 ]
Du, Junyi [1 ]
Slawin, Alexandra M. Z. [1 ]
Woollins, J. Derek [1 ]
机构
[1] Univ St Andrews, EaStCHEM Sch Chem, St Andrews KY16 9ST, Fife, Scotland
关键词
cyanamides; haloketones; selenazol-2-amines; selenoureas; Woollins' reagent; PRIMARY SELENOCARBOXYLIC AMIDES; AQUEOUS-PHASE SYNTHESIS; WOOLLINS REAGENT; PRIMARY SELENOAMIDES; FACILE PREPARATION; BETA-CYCLODEXTRIN; SELENIUM; NITRILES; 1,3-SELENAZOLE; HETEROCYCLES;
D O I
10.3390/molecules22010046
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The synthesis and X-ray single crystal structures of a series of new 4-substituted-1,3-selenazol-2-amines is reported. The efficient preparation of these compounds was carried out by two-component cyclization of the selenoureas with equimolar amounts of -haloketones. The selenoureas were obtained from the reaction of Woollins' reagent with cyanamides, followed by hydrolysis with water. All new compounds have been characterized by IR spectroscopy, multi-NMR (H-1, C-13, Se-77) spectroscopy, accurate mass measurement and single crystal X-ray structure analysis.
引用
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页数:13
相关论文
共 52 条
[1]   Electrophilic Aromatic Selenylation: New OPRT Inhibitors [J].
Abdo, Mohannad ;
Zhang, Yong ;
Schramm, Vern L. ;
Knapp, Spencer .
ORGANIC LETTERS, 2010, 12 (13) :2982-2985
[2]   DIAZOTIZATION OF A 2-AMINO-1,3-SELENAZOLE [J].
ARCHER, S ;
MCGARRY, R .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1982, 19 (05) :1245-1246
[3]  
Axelle R. C., 2002, J MED CHEM, V45, P944
[4]   A convenient procedure for the solution phase preparation of 2-aminothiazole combinatorial libraries [J].
Bailey, N ;
Dean, AW ;
Judd, DB ;
Middlemiss, D ;
Storer, R ;
Watson, SP .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (12) :1409-1414
[5]  
Bakunov SA, 2000, SYNTHESIS-STUTTGART, P1148
[6]   Novel alkylpolyaminoguanidines and alkylpolyaminobiguanides with potent antitrypanosomal activity [J].
Bi, Xiangdong ;
Lopez, Christina ;
Bacchi, Cyrus J. ;
Rattendi, Donna ;
Woster, Patrick M. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (12) :3229-3232
[7]   A novel approach to a substituted 1,3-selenazole core as a precursor of electron rich olefins:: diselenadiazafulvalene and azino-diselenadiazafulvalene [J].
Casar, Z ;
Majcen-Le Maréchal, A ;
Lorcy, D .
NEW JOURNAL OF CHEMISTRY, 2003, 27 (11) :1622-1626
[8]  
COHEN VI, 1978, SYNTHESIS-STUTTGART, P668
[9]  
Dalip K., 2011, TETRAHEDRON LETT, V52, P1983
[10]   Synthesis and multinuclear magnetic resonance investigation of some 1,3-selenazole and 1,3-selenazoline derivatives [J].
Duddeck, H ;
Bradenahl, R ;
Stefaniak, L ;
Jazwinski, J ;
Kamienski, B .
MAGNETIC RESONANCE IN CHEMISTRY, 2001, 39 (11) :709-713