Synthesis of highly functionalized pyrrole derivatives via a four-component reaction of two primary Amines and diketene in the presence of nitrostyrene

被引:34
作者
Alizadeh, Abdolali [1 ]
Rezvanian, Atieh [1 ]
Bijanzadeh, Hamid R. [1 ]
机构
[1] Tarbiat Modares Univ, Dept Chem, Tehran 18716, Iran
来源
SYNTHESIS-STUTTGART | 2008年 / 05期
关键词
amine; diketene; enaminones; nitrostyrene; pyrrole; multicomponent reaction;
D O I
10.1055/s-2008-1032168
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The one-pot synthesis of highly functionalized pyrrole derivatives from the reaction of an enaminone, which can be derived from the reaction between two primary amines and diketene, in the presence of nitrostyrene is described. The reaction occurred under neutral conditions and in excellent yields.
引用
收藏
页码:725 / 728
页数:4
相关论文
共 37 条
[1]   Synthesis of condensed heteroaromatics: novel synthesis of aminoquinolizinone derivatives as anti-HIV agents [J].
Al-Omran, F ;
Elassar, AZA ;
El-Khair, AA .
TETRAHEDRON, 2001, 57 (51) :10163-10170
[2]   A new method for the synthesis of functionalized 5-hydroxy-1,5-dihydro-2H-pyrrol-2-one:: Reaction of an enamine, derived from addition of a secondary amine to dibenzoylacetylene, with an arylsulfonyl isocyanate [J].
Alizadeh, Abdolali ;
Movahedi, Farnaz ;
Masrouri, Hassan ;
Zhu, Long-Guan .
SYNTHESIS-STUTTGART, 2006, (20) :3431-3436
[3]   A new method for the synthesis of functionalized maleimides [J].
Alizadeh, Abdolali ;
Movahedi, Farnaz ;
Esmaili, Abbas Ali .
TETRAHEDRON LETTERS, 2006, 47 (26) :4469-4471
[4]   RECENT ADVANCES IN CHEMISTRY OF PYRROLE [J].
BALTAZZI, E .
CHEMICAL REVIEWS, 1963, 63 (05) :511-+
[5]  
Bean G.P., 1990, PYRROLES 1, P105
[6]   Ionic liquid promoted synthesis of β-enamino ketones at room temperature [J].
Bhosale, RS ;
Suryawanshi, PA ;
Ingle, SA ;
Lokhande, MN ;
More, SP ;
Mane, SB ;
Bhosale, SV ;
Pawar, RP .
SYNLETT, 2006, (06) :933-935
[7]   TOTAL SYNTHESIS AND EVALUATION OF (+/-)-N-(TERT-BUTYLOXYCARBONYL)-CBI, (+/-)-CBI-CDPI1, AND (+/-)-CBI-CDPI2 - CC-1065 FUNCTIONAL AGENTS INCORPORATING THE EQUIVALENT 1,2,9,9A-TETRAHYDROCYCLOPROP[1,2-C]BENZ[1,2-E]INDOL-4-ONE (CBI) LEFT-HAND SUBUNIT [J].
BOGER, DL ;
ISHIZAKI, T ;
WYSOCKI, RJ ;
MUNK, SA ;
KITOS, PA ;
SUNTORNWAT, O .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (16) :6461-6463
[8]   Total syntheses of ningalin A, lamellarin O, lukianol A, and permethyl storniamide A utilizing heterocyclic azadiene Diels-Alder reactions [J].
Boger, DL ;
Boyce, CW ;
Labroli, MA ;
Sehon, CA ;
Jin, Q .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (01) :54-62
[9]   The structure of aromatic compounds Part II [J].
Campbell, N ;
Anderson, W ;
Gilmore, J .
JOURNAL OF THE CHEMICAL SOCIETY, 1940, :446-451
[10]   Aminovinyl ketones and aminovinyl esters as C-C-N building blocks for the synthesis of 1H-pyrrolo[3,2-e]1,2,4-triazines [J].
Charushin, VN ;
Mochulskaya, NN ;
Andreiko, AA ;
Filyakova, VI ;
Kodess, MI ;
Chupakhin, ON .
TETRAHEDRON LETTERS, 2003, 44 (11) :2421-2424