Facile regiocontrolled synthesis of trialkyl-substituted pyrazines

被引:19
作者
Elmaaty, TA [1 ]
Castle, LW [1 ]
机构
[1] Idaho State Univ, Dept Chem, Pocatello, ID 83209 USA
关键词
D O I
10.1021/ol0523751
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
alpha-Nitro ketones can be transformed selectively into trialkyl-substituted pyrazines via reaction with a-amino ketones using octyl viologen as an electron-transfer reagent. The new synthetic method, and the optimal reaction conditions that allow for the regiochemical control, are described.
引用
收藏
页码:5529 / 5530
页数:2
相关论文
共 17 条
[1]  
Barlin G. B., 1982, CHEM HETEROCYCLIC CO, V41
[2]  
BROPHY JJ, 1980, HETEROCYCLES, V14, P477
[3]   VOLATILE SECRETORY PRODUCTS OF AN AUSTRALIAN FORMICINE ANT OF THE GENUS CALOMYRMEX (HYMENOPTERA, FORMICIDAE) [J].
BROWN, WV ;
MOORE, BP .
INSECT BIOCHEMISTRY, 1979, 9 (05) :451-460
[4]  
BUCHI G, 1991, J ORG CHEM, V56, P2605
[5]   MAJOR COMPONENT OF THE TRAIL PHEROMONE OF THE LEAF-CUTTING ANT, ATTA-SEXDENS-RUBROPILOSA FOREL - 3-ETHYL-2,5-DIMETHYLPYRAZINE [J].
CROSS, JH ;
BYLER, RC ;
RAVID, U ;
SILVERSTEIN, RM ;
ROBINSON, SW ;
BAKER, PM ;
SABINODEOLIVEIRA, J ;
JUTSUM, AR ;
CHERRETT, JM .
JOURNAL OF CHEMICAL ECOLOGY, 1979, 5 (02) :187-203
[6]  
ELMAATY TA, 2005, IN PRESS MOLECULES
[7]   STRUCTURE AND SYNTHESIS OF TETRASUBSTITUTED PYRAZINES IN ANTS IN THE GENUS MESOPONERA [J].
FALES, HM ;
BLUM, MS ;
SOUTHWICK, EW ;
WILLIAMS, DL ;
ROLLER, PP ;
DON, AW .
TETRAHEDRON, 1988, 44 (16) :5045-5050
[8]   ZIRCONIUM-MEDIATED REACTIONS OF ALKYLPYRAZINES AND ALKYNES - SYNTHESIS OF HIGHLY SUBSTITUTED ALKYLPYRAZINES [J].
GURAM, AS ;
JORDAN, RF .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (22) :5994-5999
[9]   TOPOCHEMICAL PHOTOREACTIONS OF UNSYMMETRICALLY SUBSTITUTED DIOLEFINS .2. PHOTOPOLYMERIZATION OF 4'-(ALKOXYCARBONYL)-2,5-DISTYRYLPYRAZINES [J].
HASEGAWA, M ;
KATSUMATA, T ;
ITO, Y ;
SAIGO, K ;
IITAKA, Y .
MACROMOLECULES, 1988, 21 (11) :3134-3138
[10]  
MAGA JA, 1982, CRC CR REV FOOD SCI, V16, P1