Highly efficient synthesis of thioesters in water

被引:14
作者
Boeini, Hassan Zali [1 ]
Kashan, Maryam Eshghi [1 ]
机构
[1] Univ Isfahan, Dept Chem, Esfahan, Iran
关键词
COENZYME-A; ACYLATION; ALDEHYDES; VERSATILE; ALCOHOLS; ESTERS; ALDOL; BIOSYNTHESIS; REACTIVITY; CATALYSTS;
D O I
10.1039/b916852d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Thioesters were efficiently prepared via the direct reaction of tertiary thioamides and alkyl halides in water, and in the presence of catalytic amounts of NaI, hexadecyltrimethylammonium bromide (HTAB), and 1,4-diazabicyclo[2.2.2] octane (DABCO). Hence, thioamides smoothly undergo an S-alkylation with alkyl halides in aqueous media following by hydrolysis to afford the corresponding thioesters in very good to excellent yields.
引用
收藏
页码:1987 / 1991
页数:5
相关论文
共 32 条
[1]   Dess-Martin periodinane mediated synthesis of thioesters from aldehydes [J].
Bandgar, Sunita B. ;
Bandgar, B. P. ;
Korbad, B. L. ;
Sawant, S. S. .
TETRAHEDRON LETTERS, 2007, 48 (07) :1287-1290
[2]   Bromine catalyzed conversion of S-tert-butyl groups into versatile and, for self-assembly processes accessible, acetyl-protected thiols [J].
Blaszczyk, A ;
Elbing, M ;
Mayor, M .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (19) :2722-2724
[3]   Lewis acid catalyzed acylation reactions: scope and limitations [J].
Chandra, KL ;
Saravanan, P ;
Singh, RK ;
Singh, VK .
TETRAHEDRON, 2002, 58 (07) :1369-1374
[4]  
DITTMANN J, 1994, J BIOL CHEM, V269, P2841
[5]   Stereoelectronic effects dictate mechanistic dichotomy between Cu(II)-catalyzed and enzyme-catalyzed reactions of malonic acid half thioesters [J].
Fortner, Kevin C. ;
Shair, Matthew D. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (05) :1032-1033
[6]   Highly enantio- and diastereoselective boron aldol reactions of alpha-heterosubstituted thioacetates with aldehydes and silyl imines [J].
Gennari, C ;
Vulpetti, A ;
Pain, G .
TETRAHEDRON, 1997, 53 (16) :5909-5924
[7]   Synthesis and sar of thioester and thiol inhibitors of IMP-1 metallo-β-lactamase [J].
Greenlee, ML ;
Laub, JB ;
Balkovec, JM ;
Hammond, ML ;
Hammond, GG ;
Pompliano, DL ;
Epstein-Toney, JH .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (17) :2549-2554
[8]  
HAKRABORTI AK, 2004, SYNTHESIS-STUTTGART, P111
[9]   Direct ester condensation from a 1:1 mixture of carboxylic acids and alcohols catalyzed by hafnium(IV) or zirconium(IV) salts [J].
Ishihara, K ;
Nakayama, M ;
Ohara, S ;
Yamamoto, H .
TETRAHEDRON, 2002, 58 (41) :8179-8188
[10]   Thioamides as useful synthons in the synthesis of heterocycles [J].
Jagodzinski, TS .
CHEMICAL REVIEWS, 2003, 103 (01) :197-227