Elemental tellurium mediated synthesis of 2-(trifluoromethyl)oxazoles using trifluoroacetic anhydride as reagent

被引:57
作者
Luo, Beibei [1 ]
Weng, Zhiqiang [1 ]
机构
[1] Fuzhou Univ, Coll Chem, State Key Lab Photocatalysis Energy & Environm, Fuzhou 350108, Fujian, Peoples R China
基金
中国国家自然科学基金;
关键词
OXIME ACETATES; 2,5-DISUBSTITUTED OXAZOLES; N-PROPARGYLAMIDES; CYCLIZATION; STRATEGY; TRIFLUOROMETHYLATION; ALKALOIDS; CHEMISTRY; DISCOVERY;
D O I
10.1039/c8cc05670f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An elemental tellurium mediated synthesis of 2-(trifluoromethyl)oxazoles from the reaction of acetophenone oxime acetates with trifluoroacetic anhydride has been developed. This new tandem cyclization proceeds in good to excellent yields via a SET reduction followed by a 5-endo-trig pathway. Some of the title compounds showed fungicidal and insecticidal activities.
引用
收藏
页码:10750 / 10753
页数:4
相关论文
共 47 条
[1]  
Andrei A. G., 2014, CURR TOP MED CHEM, V14, P952
[2]   SCREENING OF MARINE-INVERTEBRATES FOR THE PRESENCE OF ERGOSTEROL-SENSITIVE ANTIFUNGAL COMPOUNDS [J].
ANTONIO, J ;
MOLINSKI, TF .
JOURNAL OF NATURAL PRODUCTS, 1993, 56 (01) :54-61
[3]   Preparation of 2,5-disubstituted oxazoles from N-propargylamides [J].
Arcadi, A ;
Cacchi, S ;
Cascia, L ;
Fabrizi, G ;
Marinelli, F .
ORGANIC LETTERS, 2001, 3 (16) :2501-2504
[4]   A scalable and operationally simple radical trifluoromethylation [J].
Beatty, Joel W. ;
Douglas, James J. ;
Cole, Kevin P. ;
Stephenson, Corey R. J. .
NATURE COMMUNICATIONS, 2015, 6
[5]   TRANSITION METAL-MEDIATED SYNTHESIS OF OXAZOLES [J].
Bresciani, Stefano ;
Tomkinson, Nicholas C. O. .
HETEROCYCLES, 2014, 89 (11) :2479-2543
[6]   Oxidative Trifluoromethylation and Trifluoromethylthiolation Reactions Using (Trifluoromethyl)trimethylsilane as a Nucleophilic CF3 Source [J].
Chu, Lingling ;
Qing, Feng-Ling .
ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (05) :1513-1522
[7]   OXAZOLES FROM BETA-ACYLOXY-N,N-BIS(TRIMETHYLSILYL)ENAMINES [J].
CUNICO, RF ;
KUAN, CP .
TETRAHEDRON LETTERS, 1990, 31 (14) :1945-1948
[8]   SYNTHETIC APPLICATIONS OF ORGANOTELLURIUM CHEMISTRY [J].
ENGMAN, L .
ACCOUNTS OF CHEMICAL RESEARCH, 1985, 18 (09) :274-279
[9]  
Filler R., 1993, ORGANOFLUORINE COMPO
[10]   4-(4-cycloalkyl/aryl-oxazol-5-yl)benzenesulfonamides as selective cyclooxygenase-2 inhibitors:: Enhancement of the selectivity by introduction of a fluorine atom and identification of a potent, highly selective, and orally active COX-2 inhibitor JTE-5221 [J].
Hashimoto, H ;
Imamura, K ;
Haruta, J ;
Wakitani, K .
JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (07) :1511-1517