One-step synthesis of polysubstituted benzene derivatives by multi-component cyclization of α-bromoacetate, malononitrile and aromatic aldehydes

被引:84
作者
Yan, Chao Guo [1 ]
Song, Xiao Kai [1 ]
Wang, Qi Fang [1 ]
Sun, Jing [1 ]
Siemeling, Ulrich [2 ]
Bruhn, Clemens [2 ]
机构
[1] Yangzhou Univ, Coll Chem & Chem Engn, Yangzhou 225002, Peoples R China
[2] Univ Kassel, Inst Chem, D-34132 Kassel, Germany
关键词
D O I
10.1039/b718171j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Polysubstituted benzene derivatives with an unprecedented substitution pattern are produced in a novel one-pot multi-component cyclization reaction from pyridine, ethyl alpha-bromoacetate, malononitrile and aromatic aldehyde in refluxing acetonitrile.
引用
收藏
页码:1440 / 1442
页数:3
相关论文
共 55 条
[11]   ELECTROCHEMICAL TRANSFORMATION OF CYANOACETIC ESTER AND ALDEHYDES INTO 3-SUBSTITUTED 1,2-DICYANOCYCLOPROPANE-1,2-DICARBOXYLATES [J].
ELINSON, MN ;
LIZUNOVA, TL ;
UGRAK, BI ;
DEKAPRILEVICH, MO ;
NIKISHIN, GI ;
STRUCHKOV, YT .
TETRAHEDRON LETTERS, 1993, 34 (36) :5795-5798
[12]   One-step synthesis of heterocyclic privileged medicinal scaffolds by a multicomponent reaction of malononitrile with aldehydes and thiols [J].
Evdokimov, Nikolai M. ;
Kireev, Artem S. ;
Yakovenko, Andrey A. ;
Antipin, Mikhail Yu. ;
Magedov, Igor V. ;
Kornienko, Alexander .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (09) :3443-3453
[13]   One-step, three-component synthesis of pyridines and 1,4-dihydropyridines with manifold medicinal utility [J].
Evdokimov, NM ;
Magedov, IV ;
Kireev, AS ;
Kornienko, A .
ORGANIC LETTERS, 2006, 8 (05) :899-902
[14]  
FATIADI AJ, 1978, SYNTHESIS-STUTTGART, P241
[15]   CHEMISTRY OF MALONONITRILE [J].
FREEMAN, F .
CHEMICAL REVIEWS, 1969, 69 (05) :591-+
[16]   One-pot synthesis of 3-carboxycoumarins via consecutive knoevenagel and pinner reactions in water [J].
Fringuelli, F ;
Piermatti, O ;
Pizzo, F .
SYNTHESIS-STUTTGART, 2003, (15) :2331-2334
[17]   Synthesis, antimicrobial activity and conformational analysis of novel substituted pyridines:: BF3-promoted reaction of hydrazine with 2-alkoxy pyridines [J].
Goda, FE ;
Abdel-Aziz, AAM ;
Attef, OA .
BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (08) :1845-1852
[18]  
GOSSELCK J, 1969, TETRAHEDRON LETT, P2615
[19]   Mechanistic studies leading to a new procedure for rapid, microwave assisted generation of pyridine-3,5-dicarbonitrile libraries [J].
Guo, Kai ;
Thompson, Mark J. ;
Reddy, Tummala R. K. ;
Mutter, Roger ;
Chen, Beining .
TETRAHEDRON, 2007, 63 (24) :5300-5311
[20]   Thiourea-catalyzed asymmetric Michael addition of activated methylene compounds to α,β-unsaturated imides:: Dual activation of imide by intra- and intermolecular hydrogen bonding [J].
Inokuma, Tsubasa ;
Hoashi, Yasutaka ;
Takemoto, Yoshiji .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (29) :9413-9419