AgBF4/[Bmim]BF4-Catalyzed [3+2] Cycloaddition of Cyclic Diazodicarbonyl Compounds: Efficient Synthesis of 2,3-Dihydrofurans and Conversion to 3-Acylfurans

被引:10
作者
Xia, Likai [1 ]
Lee, Yong Rok [1 ]
Kim, Sung Hong [2 ]
Lyoo, Won Seok [3 ]
机构
[1] Yeungnam Univ, Sch Chem Engn, Kyongsan 712749, South Korea
[2] Korea Basic Sci Inst, Daegu Ctr, Anal Res Div, Taegu 702701, South Korea
[3] Yeungnam Univ, Sch Text, Kyongsan 712749, South Korea
关键词
AgBF4/[Bmim]BF4; 3+2] cycloaddition; Diazodicarbonyls; 2,3-Dihydrofurans; SILVER-CATALYZED REACTIONS; ACETATE-MEDIATED ADDITION; BETA-DICARBONYL COMPOUNDS; ONE-POT SYNTHESIS; 1,3-DICARBONYL COMPOUNDS; MANGANESE(III) ACETATE; OXIDATIVE ADDITION; REGIOSELECTIVE SYNTHESIS; DERIVATIVES; ALKENES;
D O I
10.5012/bkcs.2011.32.5.1554
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel and efficient method for the synthesis of 2,3-dihydrofurans bearing a variety of substituents on the dihydrofuran ring was achieved by the reaction of cyclic diazodicarbonyl compounds with styrene and vinyl acetate. The key strategy was AgBF4/[Bmim]BF4-catalyzed [3+2] cycloaddition. The synthesized dihydrofurans with an acetate group were further converted to the corresponding 3-acylfurans.
引用
收藏
页码:1554 / 1558
页数:5
相关论文
共 44 条
[1]  
Alexiou I, 1999, SYNLETT, P1925
[2]   Manganese(III)-mediated oxidative free-radical additions of 1,3-dicarbonyl compounds to homobenzonorbornadiene and benzobarrelene: mechanistic studies [J].
Ali, Mohamed Fadelalla ;
Caliskan, Rasit Ali ;
Sahin, Ertan ;
Balci, Metin .
TETRAHEDRON, 2009, 65 (07) :1430-1437
[3]   Silver-mediated synthesis of heterocycles [J].
Alvarez-Corral, Miriam ;
Munoz-Dorado, Manuel ;
Rodirguez-Garcia, Ignacio .
CHEMICAL REVIEWS, 2008, 108 (08) :3174-3198
[4]   FURANNULATION STRATEGY FOR SYNTHESIS OF THE NATURALLY-OCCURRING FUSED 3-METHYLFURANS - EFFICIENT SYNTHESIS OF EVODONE AND MENTHOFURAN AND REGIOSELECTIVE SYNTHESIS OF MATURONE VIA A LEWIS-ACID CATALYZED DIELS-ALDER REACTION - SOME COMMENTS FOR ITS MECHANISTIC ASPECTS [J].
ASO, M ;
OJIDA, A ;
YANG, G ;
CHA, OJ ;
OSAWA, E ;
KANEMATSU, K .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (15) :3960-3968
[5]   [3+2]-cycloaddition reactions of 2-phenyliodonio-1,3-dioxacyclohexanemethylide: Facile synthesis of fused dihydrofuran derivatives [J].
Asouti, A ;
Hadjiarapoglou, LP .
TETRAHEDRON LETTERS, 1998, 39 (49) :9073-9076
[6]   Synthesis of 3-aryl-2-benzoylbenzofuran derivatives using manganese(III) acetate-mediated addition of dimedon to chalcone derivatives [J].
Ceylan, Mustafa ;
Findik, Esra .
SYNTHETIC COMMUNICATIONS, 2008, 38 (07) :1070-1077
[7]  
Chen FE, 2000, SYNTHESIS-STUTTGART, P1091
[8]  
Davies H.M. L., 2001, ORG REACT, V57, P1, DOI DOI 10.1002/0471264180.OR057.01
[9]  
Dean F.M., 1984, Comprehensive Heterocyclic Chemistry, V4, P531, DOI [10.1016/B978-008096519-2.00060-6, DOI 10.1016/B978-008096519-2.00060-6]
[10]   RECENT ADVANCES IN FURAN CHEMISTRY .1. [J].
DEAN, FM .
ADVANCES IN HETEROCYCLIC CHEMISTRY, 1982, 30 :167-238