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
[11]   One-pot synthesis of 2-sulfanyl-3-sulfinyl(or sulfonyl)-1H-indoles via cyclization of 1-isothiocyanato-2-[sulfinyl(or sulfonyl)methyl]benzenes with sodium hydride [J].
Kobayashi, Kazuhiro ;
Kobayashi, Akihiro ;
Ezaki, Kosuke .
TETRAHEDRON, 2013, 69 (37) :7936-7942
[12]   One-Pot Synthesis of 3-Arylquinazoline-2,4(1H, 3H)-dithiones by the Reaction of 2-Lithiophenyl Isothiocyanates with Aryl Isothiocyanates [J].
Kobayashi, Kazuhiro ;
Yokoi, Yuki ;
Konishi, Hisatoshi .
SYNTHESIS-STUTTGART, 2011, (10) :1526-1528
[13]   CRYSTAL AND MOLECULAR-STRUCTURE OF DYNEMICIN-A - A NOVEL 1,5-DIYN-3-ENE ANTITUMOR ANTIBIOTIC [J].
KONISHI, M ;
OHKUMA, H ;
TSUNO, T ;
OKI, T ;
VANDUYNE, GD ;
CLARDY, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (09) :3715-3716
[14]  
KUMAR A, 1980, SYNTHESIS-STUTTGART, P748
[15]  
NAKANISHI KOJI, 1967, PURE APPL CHEM, V14, P89, DOI 10.1351/pac196714010089
[16]   Rapid Construction of the Aza-Propellane Core of Acutumine via a Photochemical [2+2] Cycloaddition Reaction [J].
Navarro, Raul ;
Reisman, Sarah E. .
ORGANIC LETTERS, 2012, 14 (17) :4354-4357
[17]  
Nicolaou KC, 2002, ANGEW CHEM INT EDIT, V41, P1668, DOI 10.1002/1521-3773(20020517)41:10<1668::AID-ANIE1668>3.0.CO
[18]  
2-Z
[19]   GINKGOLIDES [J].
OKABE, K ;
YAMADA, K ;
YAMAMURA, S ;
TAKADA, S .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1967, (21) :2201-&
[20]   Synthesis of propellane-containing natural products [J].
Pihko, AJ ;
Koskinen, AAP .
TETRAHEDRON, 2005, 61 (37) :8769-8807