Regioselective Multicomponent Sequential Synthesis of Oxa-Aza[3.3.3]propellanes

被引:16
作者
Alizadeh, Abdolali [1 ]
Bayat, Fahimeh [1 ]
Zhu, Long-Guan [2 ]
机构
[1] Tarbiat Modares Univ, Dept Chem, Tehran, Iran
[2] Zhejiang Univ, Dept Chem, Hangzhou 310027, Peoples R China
关键词
POLARIZED KETENE S; S-ACETALS; CONVENIENT SYNTHESIS; CYCLIZATION; S; N-ACETALS; PROPELLANES; POT;
D O I
10.1071/CH13654
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A concise and efficient sequential four-component approach to oxa-aza[3.3.3]propellanes has been developed by reaction of aryl isothiocyanates, malonate compounds, ninhydrin, and malononitrile in the presence of NaH in DMF. The value of this method lies in its regioselectivity, good yields, lack of a metal-catalyst, ease of handling, and creating five new bonds in one operation. No inert atmosphere or separation by column chromatography is necessary.
引用
收藏
页码:949 / 952
页数:4
相关论文
共 28 条
[1]   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
[2]  
Alizadeh A, 2011, HELV CHIM ACTA, V94, P1802
[3]   Manganese(III)-based dioxapropellane synthesis using tricarbonyl compounds [J].
Asahi, Kentaro ;
Nishino, Hiroshi .
TETRAHEDRON, 2008, 64 (08) :1620-1634
[4]   THIOPHENES VIA S-ALKYLATION [J].
AUGUSTIN, M ;
RUDORF, WD ;
SCHMIDT, U .
TETRAHEDRON, 1976, 32 (24) :3055-3061
[5]  
CHAKRASALI RT, 1988, SYNTHESIS-STUTTGART, P453
[6]   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-&
[7]   STRUCTURE OF FRENOLICIN [J].
ELLESTAD, GA ;
KUNSTMANN, MP ;
WHALEY, HA ;
PATTERSON, EL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (05) :1325-+
[8]   SYNTHESIS AND REARRANGEMENT OF DISPIRO[3.1.3.2]UNDECANES, DISPIRO[3.0.3.3]UNDECANES AND DISPIRO[3.0.4.2]UNDECANES - NEW ENTRIES TO [3.3.3]PROPELLANES [J].
FITJER, L ;
KANSCHIK, A ;
MAJEWSKI, M .
TETRAHEDRON, 1994, 50 (37) :10867-10878
[9]  
GINSBURG D, 1987, TOP CURR CHEM, V137, P1
[10]   PROPELLANES .11. SYNTHESIS OF DIOXA[4.3.3]PROPELLANES FROM VICINAL TETRAKIS(HYDROXYMETHYL)CYCLOALKANES [J].
JAMROZIK, J ;
JAMROZIK, M ;
SCIBOROWICZ, P ;
ZESLAWSKI, W .
MONATSHEFTE FUR CHEMIE, 1995, 126 (05) :587-591