Highly efficient synthesis of 2,5-disubstituted pyrazines from (Z)-β-haloenol acetates

被引:13
作者
Chen, Zhengwang [1 ]
Ye, Dongnai [1 ]
Xu, Guohai [1 ]
Ye, Min [1 ]
Liu, Liangxian [1 ]
机构
[1] Gannan Normal Univ, Sch Chem & Chem Engn, Ganzhou 341000, Peoples R China
关键词
ONE-POT SYNTHESIS; ARYL HALIDES; FUNCTIONALIZATION; IDENTIFICATION; CONDENSATION; SUBSTITUENTS; DERIVATIVES; AMINATION; NITROGEN; RING;
D O I
10.1039/c3ob41164h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly efficient synthesis of a wide range of 2,5-disubstituted pyrazines from (Z)-beta-haloenol acetates is described. The reactions are conducted under convenient conditions and provide products with excellent regioselectivity in moderate to excellent yields with a broad substrate scope, including a variety of aromatic and aliphatic haloenol acetates.
引用
收藏
页码:6699 / 6702
页数:4
相关论文
共 62 条
[1]   Reductive decyanation of pyrazinecarbonitriles [J].
Albaneze-Walker, J ;
Zhao, M ;
Baker, MD ;
Dormer, PG ;
McNamara, J .
TETRAHEDRON LETTERS, 2002, 43 (38) :6747-6750
[2]   Straightforward access to pyrazines, piperazinones, and quinoxalines by reactions of 1,2-diaza-1,3-butadienes with 1,2-diamines under solution, solvent-free, or solid-phase conditions [J].
Aparicio, Domitila ;
Attanasi, Orazio A. ;
Filippone, Paolino ;
Ignacio, Roberto ;
Lillini, Samuele ;
Mantellini, Fabio ;
Palacios, Francisco ;
Santos, Jesus M. de los .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (16) :5897-5905
[3]  
Barlin G. B., 1982, CHEM HETEROCYCLIC CO, V41
[4]   Radical chain reactions of α-azido ketones with tributyltin hydride:: reduction vs nitrogen insertion and 1,2-hydrogen shift in the intermediate N-stannylaminyl radicals [J].
Benati, L ;
Leardini, R ;
Minozzi, M ;
Nanni, D ;
Spagnolo, P ;
Strazzari, S ;
Zanardi, G ;
Calestani, G .
TETRAHEDRON, 2002, 58 (18) :3485-3492
[5]  
BUCHI G, 1991, J ORG CHEM, V56, P2605
[6]   A planning strategy for diversity-oriented synthesis [J].
Burke, MD ;
Schreiber, SL .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (01) :46-58
[7]   Synthesis of pyrazine alealoids from Botryllus leachi.: Diazines 43 [J].
Buron, F ;
Plé, N ;
Turck, A ;
Queguiner, G .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (07) :2616-2621
[8]   Towards a biomimetic synthesis of barrenazine A [J].
Buron, Frederic ;
Turck, Alain ;
Plé, Nelly ;
Bischoff, Laurent ;
Marsais, Francis .
TETRAHEDRON LETTERS, 2007, 48 (25) :4327-4330
[9]   New approach to asymmetrically substituted methoxypyrazines, derivatives of wine flavors [J].
Candelon, Nicolas ;
Shinkaruk, Svitlana ;
Bennetau, Bernard ;
Bennetau-Pelissero, Catherine ;
Dumartin, Marie-Laurence ;
Degueil, Marie ;
Babin, Pierre .
TETRAHEDRON, 2010, 66 (13) :2463-2469
[10]  
Caradoc-Davies P.L., 2001, DALTON T, P2749