A simple and efficient synthesis of 2-methyl-2-trifluoromethylchroman-4-ones from 2-trifluoromethyl-4H-chromen-4-imines and malonic acid

被引:8
作者
Sosnovskikh, VY [1 ]
Usachev, BI [1 ]
机构
[1] Ural State Univ, Dept Chem, Ekaterinburg 620083, Russia
来源
SYNTHESIS-STUTTGART | 2002年 / 16期
关键词
N-benzyl-2-trifluoromethyl-4H-chromen-4-imines; malonic acid; 2-methyl-2-trifluoromethylchroman-4-ones; oxidation; fluorinated analogues of natural compounds;
D O I
10.1055/s-2002-35233
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
N-Benzyl-2-trifluoromethyl-4H-chromen-4-imines and malonic acid on heating in anhydrous dioxane afford 2-trifluoromethyl-2-methylchroman-4-ones in similar to60% yield. 2-Methyl-2-trifluoromethyl-4-oxochromane-6-carbaidehyde and 2-methyl-2-trifluoromethyl-4-oxochromane-6-carboxylic acid, the fluorinated analogues of natural lactarochromal and the corresponding acid, were obtained by the oxidation of 2,6-climethyl-2-trifluoromethylchroman-4-one with K2S2O8.
引用
收藏
页码:2341 / 2343
页数:3
相关论文
共 17 条
[1]   AROMATIC-COMPOUNDS FROM LIQUID CULTURES OF LACTARIUS-DELICIOSUS [J].
AYER, WA ;
TRIFONOV, LS .
JOURNAL OF NATURAL PRODUCTS, 1994, 57 (06) :839-841
[2]  
BANERJI A, 1984, INDIAN J CHEM B, V23, P885
[3]   NMR SPECTRA OF INTRAMOLECULARLY HYDROGEN-BONDED COMPOUNDS .2. SCHIFF BASES OF BETA-DIKETONES AND O-HYDROXYCARBONYL COMPOUNDS [J].
BROWN, NMD ;
NONHEBEL, DC .
TETRAHEDRON, 1968, 24 (16) :5655-&
[4]   SYNTHESIS OF 2-SUBSTITUTED CHROMONES, CHROMANONES, AND THEIR THIO ANALOGS USING ORGANOCOPPER REAGENTS [J].
CLARKE, PD ;
FITTON, AO ;
SUSCHITZKY, H ;
WALLACE, TW ;
DOWLATSHAHI, HA ;
SUSCHITZKY, JL .
TETRAHEDRON LETTERS, 1986, 27 (01) :91-94
[5]   Electrolytic partial fluorination of organic compounds. 55. Highly regio- and stereoselective anodic monofluorination of 2,3-dihydrochroman-4-one and chromone derivatives [J].
Dawood, KM ;
Fuchigami, T .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (23) :7691-7695
[6]  
Ellis G. P., 1977, CHEM HETEROCYCLIC CO, V31, P1, DOI DOI 10.1002/9780470187012.CHL
[7]  
Kamat VP, 2001, J CHEM RES-S, P41
[8]  
Ngo L.V., 1981, PHYTOCHEMISTRY, V20, P485
[9]   SYNTHESIS AND ANTIALLERGIC ACTIVITY OF 11-(AMINOALKYLIDENE)-6,11-DIHYDRODIBENZ[B,E]OXEPIN DERIVATIVES [J].
OHSHIMA, E ;
OTAKI, S ;
SATO, H ;
KUMAZAWA, T ;
OBASE, H ;
ISHII, A ;
ISHII, H ;
OHMORI, K ;
HIRAYAMA, N .
JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (11) :2074-2084
[10]   CONJUGATE ADDITION OF CUPRATE REAGENTS TO CHROMONES - A ROUTE TO 2-SUBSTITUTED CHROMAN-4-ONES [J].
SAENGCHANTARA, ST ;
WALLACE, TW .
TETRAHEDRON, 1990, 46 (08) :3029-3036