Efficient synthesis of thioesters and amides from aldehydes by using an intermolecular radical reaction in water

被引:57
作者
Nambu, H [1 ]
Hata, K [1 ]
Matsugi, M [1 ]
Kita, Y [1 ]
机构
[1] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan
关键词
aldehydes; amidation; radical reactions; surfactants; thioesters;
D O I
10.1002/chem.200400754
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The combination of the water-soluble radical initiator, 2,2'-azobis[2-(2-imidazolin-2-yl)propane] dihydrochloride (VA-044) and the surfactant, cetyltrimethyl-ammonium bromide (CTAB), was found to be the most suitable condition for the effective and direct synthesis of useful active thioesters (pentafluorophenyl thioesters) in water. In addition, the direct amidation of aldehydes was achieved by the addition of the amines to the thioesterification reaction mixture in water.
引用
收藏
页码:719 / 727
页数:9
相关论文
共 110 条
[1]   A solid supported synthesis of thiol esters [J].
Adamczyk, M ;
Fishpaugh, JR .
TETRAHEDRON LETTERS, 1996, 37 (25) :4305-4308
[2]   Catalytic crossed Michael cycloisomerization of thioenoates:: Total synthesis of (±)-ricciocarpin A [J].
Agapiou, K ;
Krische, MJ .
ORGANIC LETTERS, 2003, 5 (10) :1737-1740
[3]   Application of the chiral acyl anion equivalent, trans-1,3-dithiane 1,3-dioxide, to an asymmetric synthesis of (R)-salbutamol [J].
Aggarwal, VK ;
Esquivel-Zamora, BN .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (24) :8618-8621
[4]   COBALT(II) CHLORIDE CATALYZED COUPLING OF THIOLS AND ANHYDRIDES - A NEW AND EFFICIENT SYNTHESIS OF THIOL ESTERS [J].
AHMAD, S ;
IQBAL, J .
TETRAHEDRON LETTERS, 1986, 27 (32) :3791-3794
[5]  
ALVAREZIBARRA C, 1989, SYNTHESIS-STUTTGART, P560
[6]   GENERAL KETONE SYNTHESIS - REACTION OF ORGANOCOPPER REAGENTS WITH S-ALKYL AND S-ARYL THIOESTERS [J].
ANDERSON, RJ ;
HENRICK, CA ;
ROSENBLU.LD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (11) :3654-3655
[7]   ENANTIOSELECTIVE ONE-POT SYNTHESIS OF BETA-LACTAMS FROM ACHIRAL 2-PYRIDYLTHIOESTERS AND AROMATIC IMINES [J].
ANNUNZIATA, R ;
BENAGLIA, M ;
CINQUINI, M ;
COZZI, F .
TETRAHEDRON LETTERS, 1995, 36 (04) :613-616
[8]   DIASTEREOSELECTIVE ALDOL CONDENSATION OF DIRECTLY GENERATED TITANIUM ENOLATES OF ACTIVATED ESTERS [J].
ANNUNZIATA, R ;
CINQUINI, M ;
COZZI, F ;
COZZI, PG ;
CONSOLANDI, E .
TETRAHEDRON, 1991, 47 (37) :7897-7910
[9]   AN IMPROVED AND SIMPLE SYNTHESIS OF METHYL OR ETHYL 7-OXOHEPTANOATE AND 7-ACETOXYHEPTANAL [J].
BALLINI, R ;
MARCANTONI, E ;
PETRINI, M .
SYNTHETIC COMMUNICATIONS, 1991, 21 (8-9) :1075-1081
[10]  
BANERJI A, 1989, J INDIAN CHEM SOC, V66, P664