Chemoselective Synthesis of Novel Heterocyclic [3.3.3]Propellane Derivatives via a One-pot Three-component Reaction

被引:12
作者
Wang, Jing [1 ]
Liu, Hongzhi [1 ]
Wen, Ren [1 ]
Li, Jie [2 ]
Zhu, Songlei [1 ]
机构
[1] Xuzhou Med Univ, Dept Chem, Sch Pharm, Xuzhou 221004, Jiangsu, Peoples R China
[2] Zhengda Tianqing Pharmaceut Grp Co LTD, Lianyungang 222062, Jiangsu, Peoples R China
关键词
acenaphthenequinone; oxa-aza[3.3.3]propellane; chemoselectivity; multi-component reaction; MULTICOMPONENT REACTIONS; PROPELLANES; EFFICIENT;
D O I
10.1002/cjoc.201700103
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A highly chemoselective method for the synthesis of heterocyclic [3.3.3]propellane derivatives was developed via sequential three-component reactions of acenaphthenequinone, malononitrile/cyanoacetate and a variety of 1,3-dicarbonyl compounds under mild conditions in ethanol. A plausible mechanism for this type of reaction was proposed. The value of this method was highlighted by its high selectivity, simple procedures, and good yields.
引用
收藏
页码:1463 / 1468
页数:6
相关论文
共 36 条
[1]   Tandem One-Pot Synthesis of Indoles Having a Structural Moiety of Propellane [J].
Alizadeh, Abdolali ;
Bayat, Fahimeh ;
Sadeghi, Vahideh .
LETTERS IN ORGANIC CHEMISTRY, 2015, 12 (03) :153-158
[2]   Regioselective Multicomponent Sequential Synthesis of Oxa-Aza[3.3.3]propellanes [J].
Alizadeh, Abdolali ;
Bayat, Fahimeh ;
Zhu, Long-Guan .
AUSTRALIAN JOURNAL OF CHEMISTRY, 2014, 67 (06) :949-952
[3]   Highly Convergent One-Pot Four-Component Regioselective Synthesis of Spiro-pyranopyrazoles and Oxa-aza-[3.3.3]propellanes [J].
Alizadeh, Abdolali ;
Bayat, Fahimeh .
HELVETICA CHIMICA ACTA, 2014, 97 (05) :694-700
[4]   Synthesis of Heterocyclic [3.3.3]Propellanes via a Sequential Four-Component Reaction [J].
Alizadeh, Abdolali ;
Rezvanian, Atieh ;
Zhu, Long-Guan .
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (09) :4385-4390
[5]   Manganese(III)-based dioxapropellane synthesis using tricarbonyl compounds [J].
Asahi, Kentaro ;
Nishino, Hiroshi .
TETRAHEDRON, 2008, 64 (08) :1620-1634
[6]  
Diels O, 1931, LIEBIGS ANN CHEM, V486, P191
[7]   Recent developments in isocyanide based multicomponent reactions in applied chemistry [J].
Dömling, A .
CHEMICAL REVIEWS, 2006, 106 (01) :17-89
[8]   Chemistry and Biology Of Multicomponent Reactions [J].
Domling, Alexander ;
Wang, Wei ;
Wang, Kan .
CHEMICAL REVIEWS, 2012, 112 (06) :3083-3135
[9]   TERPENOIDS .14. CONSTITUTION AND BIOGENESIS OF MARASMIC ACID [J].
DUGAN, JJ ;
DEMAYO, P ;
NISBET, M ;
ROBINSON, JR ;
ANCHEL, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (12) :2838-&
[10]   STRUCTURE OF FRENOLICIN [J].
ELLESTAD, GA ;
KUNSTMANN, MP ;
WHALEY, HA ;
PATTERSON, EL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (05) :1325-+