Synthesis of 1,2,4-Triazolines and Triazoles Utilizing Oxazolones

被引:29
作者
Saleem, Rahman Shah Zaib [1 ]
Tepe, Jetze J. [1 ]
机构
[1] Michigan State Univ, Dept Chem, E Lansing, MI 48823 USA
关键词
N-SUBSTITUTED PYRROLES; DIELS-ALDER REACTION; 1,3-DIPOLAR CYCLOADDITIONS; DIETHYL AZODICARBOXYLATE; MUNCHNONES; 4-PHENYL-3H-1,2,4-TRIAZOLE-3,5(4H)-DIONE; DERIVATIVES; ACCESS; ROUTE;
D O I
10.1021/jo100716m
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We describe herein a convenient method for the synthesis of 1,2,4-triazolines using oxazolones and azodicarboxylates. Subsequent treatment of these 1,2,4-triazolines with NaOH provides efficient access to the corresponding triazoles.
引用
收藏
页码:4330 / 4332
页数:3
相关论文
共 40 条
[1]   THE REACTION OF IMIDAZO[1,5-A]PYRIDINES WITH METHYLTRIAZOLINEDIONES AND PHENYLTRIAZOLINEDIONES AND WITH DIETHYL AZODICARBOXYLATE [J].
ANDERSON, DJ ;
WATT, W .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1995, 32 (05) :1525-1530
[2]  
[Anonymous], 2006, TURK J CHEM
[3]   Solid-supported synthesis of imidazoles: A strategy for direct resin-attachment to the imidazole core [J].
Bilodeau, MT ;
Cunningham, AM .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (09) :2800-2801
[4]   1.3-DIPOLAR CYCLOADDITIONS .61. CYCLOADDITIONS OF N-SUBSTITUTED OXAZOLIUM-5-OLATES TO NITRILES, NITRO, NITROSO AND AZO COMPOUNDS [J].
BRUNN, E ;
FUNKE, E ;
GOTTHARD.H ;
HUISGEN, R .
CHEMISCHE BERICHTE-RECUEIL, 1971, 104 (05) :1562-&
[5]   5(4H)-oxazolones.: Part XI.: Cycloaddition reaction of oxazolones and munchnones to triphenylvinylphosphonium salts as synthetic equivalents of alkynes. [J].
Clerici, F ;
Gelmi, ML ;
Trimarco, P .
TETRAHEDRON, 1998, 54 (21) :5763-5774
[6]   1,2,4-triazolo mercapto and aminonitriles as potent antifungal agents [J].
Collin, X ;
Sauleau, A ;
Coulon, J .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (15) :2601-2605
[7]  
CONSONNI R, 1991, J CHEM RES-S, P188
[8]   [2+2] Cycloaddition reactions of imines with cyclic ketenes:: Synthesis of 1,3-thiazolidine derived spiro-β-lactams and their transformations [J].
Cremonesi, G ;
Dalla Croce, P ;
La Rosa, C .
HELVETICA CHIMICA ACTA, 2005, 88 (06) :1580-1588
[9]  
De Clercq E, 2004, J CLIN VIROL, V30, P115, DOI [10.1016/j.jcv.2004.02.009, 10.1002/rmv.439]
[10]   The diverse chemistry of oxazol-5-(4H)-ones [J].
Fisk, Jason S. ;
Mosey, Robert A. ;
Tepe, Jetze J. .
CHEMICAL SOCIETY REVIEWS, 2007, 36 (09) :1432-1440