Expedient synthesis of pyrrolo[1,2-a]quinoxalines through one-pot three-component reactions of o-phenylenediamines, 2-alkoxy-2,3-dihydrofurans and ketones

被引：12
作者：
Wang, Man [1 ]
Liu, Changhui [1 ]
Gu, Yanlong [1 ,2 ]
机构：
[1] Huazhong Univ Sci & Technol, Sch Chem & Chem Engn, Minist Educ, Key Lab Large Format Battery Mat & Syst, Wuhan 430074, Peoples R China
[2] Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China
来源：
TETRAHEDRON | 2016年 / 72卷 / 43期
基金：
中国国家自然科学基金;
关键词：
Pyrrolo[1,2-a]quinoxaline; Three-component reaction; 1,5-Bisnucleophile; Pictet-Spengler reaction; COPPER-CATALYZED ANNULATION; POTENTIAL INHIBITORS; QUINOXALINE DERIVATIVES; ANTIMALARIAL ACTIVITY; RECEPTOR ANTAGONISTS; ACID CATALYST; PART II; EFFICIENT; FURANS; ACETYLENEDICARBOXYLATES;
D O I：
10.1016/j.tet.2016.09.014
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Pyrrolo[1,2-a]quinoxalines were synthesized through a three-component reaction of 2-alkoxy-2,3-dihydrofuran, o-phenylenediamine and ketone. This reaction was performed in nitromethane by using boron trifluoride etherate as catalyst. Mechanism of this reaction involves the following two steps: (i) a condensation reaction of the dihydrofuran with o-phenylenediamine, which produced a N-(2-aminophenyl)pyrrole derivative that can act as a 1,5-bisnucleophile, and (ii) an intramolecular Mannich-type reaction of the bisnucleophile and, ketone to produce the pyrrolo[1,2-a]quinoxaline derivative. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6854 / 6865
页数：12
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