Synthesis of new 3-cyanoacetamide pyrrole and 3-acetonitrile pyrrole derivatives

被引:34
作者
Bayat, Mohammad [1 ]
Nasri, Shima [1 ]
Notash, Behrouz [2 ]
机构
[1] Imam Khomeini Int Univ, Dept Chem, Qazvin, Iran
[2] Shahid Beheshti Univ, Dept Chem, GC, Tehran 1983963113, Iran
关键词
Aryl glyoxal; One-pot four-component reaction; Fused pyrrole; 3-Cyanoacetamide pyrrole; 3-Acetonitrile pyrrole; FACILE;
D O I
10.1016/j.tet.2017.02.005
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new fused heterocyclic derivatives of pyrrole containing acetonitrile or cyanoacetonitrile moiety at 3-position is described by a one-pot multicomponent reaction. The reaction of dimedone, various aniline, aryl glyoxal with malononitrile/ethyl cyanoacetate/methyl cyanoacetate under mild conditions. The present method does not involve any hazardous organic solvents or catalysts. The significant features of this method are readily available starting materials, good yields, and easy purification. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1522 / 1527
页数:6
相关论文
共 21 条
[1]  
Almerico A. W., 2000, ARKIVOC, V4, P486
[2]   A facile and effective synthesis of 4-imino-3-(arylidene)- azetidine-2-thiones via phosphorus pentasulfide [J].
Amiri, Ouafa ;
Rakib, El Mostapha ;
Abdelouahid, Medaghri-Alaoui ;
Faustino, Maria A. F. ;
Neves, Maria G. P. M. S. ;
Cavaleiro, Jose A. S. .
JOURNAL OF SULFUR CHEMISTRY, 2015, 36 (01) :9-15
[3]   Simple synthesis of benzo[g]imidazo[1,2-a]quinolinedione derivatives via a one-pot, four-component reaction [J].
Bayat, Mohammad ;
Hosseini, Fahimeh ;
Notash, Behrouz .
TETRAHEDRON LETTERS, 2016, 57 (49) :5439-5441
[4]   An Efficient One-Pot Synthesis of Bis Butenolides [J].
Bayat, Mohammad ;
Fox, Joseph M. .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2016, 53 (05) :1661-1664
[5]   Pyrrole: a resourceful small molecule in key medicinal hetero-aromatics [J].
Bhardwaj, Varun ;
Gumber, Divya ;
Abbot, Vikrant ;
Dhiman, Saurabh ;
Sharma, Poonam .
RSC ADVANCES, 2015, 5 (20) :15233-15266
[6]   Polysubstituted pyrrole derivatives via 1,2-alkenyl migration of novel γ-amino-α,β-unsaturated aldehydes and α-diazocarbonyls [J].
Cai, Shuting ;
Zeng, Jing ;
Li, Yongxin ;
Liu, Xue-Wei .
RSC ADVANCES, 2014, 4 (14) :7275-7278
[7]   Aroyl(aminoacyl)pyrroles, a new class of anticonvulsant agents [J].
Carson, JR ;
Carmosin, RJ ;
Pitis, PM ;
Vaught, JL ;
Almond, HR ;
Stables, JP ;
Wolf, HH ;
Swinyard, EA ;
White, HS .
JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (11) :1578-1584
[8]   Multicomponent reactions for the synthesis of pyrroles [J].
Estevez, Veronica ;
Villacampa, Mercedes ;
Carlos Menendez, J. .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (11) :4402-4421
[9]  
Gribble G.W., 1996, COMPREHENSIVE HETERO, V2, P207, DOI DOI 10.1016/B978-008096518-5.00043-5
[10]  
Hantzsch A., 1890, BER DTSCH CHEM GES, V23, P1474, DOI [DOI 10.1002/CBER.189002301243, 10.1002/cber.189002301243]