An Efficient Synthesis of Pyrrolo[1,2-a]quinoxalines by CopperCatalyzed C-H Activation of Arylacetic Acids

被引:35
作者
Lade, Jatin J. [1 ]
Patil, Bhausaheb N. [1 ]
Vhatkar, Mahendra V. [1 ]
Vadagaonkar, Kamlesh S. [2 ]
Chaskar, Atul C. [1 ,2 ]
机构
[1] Univ Mumbai, Natl Ctr Nanosci & Nanotechnol, Kalina Campus, Bombay 400098, Maharashtra, India
[2] Inst Chem Technol, Dept Dyestuff Technol, Nathalal Parekh Marg, Bombay 400019, Maharashtra, India
关键词
arylacetic acid; C-H activation; copper; pyrroles; quinoxalines; REGIOSELECTIVE SYNTHESIS; ANTIMALARIAL ACTIVITY; POTENTIAL INHIBITORS; BRONSTED ACID; DERIVATIVES;
D O I
10.1002/ajoc.201700239
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient and convenient synthesis of pyrrolo[1,2-a]quinoxalines from 1-(2-aminoaryl) pyrrole and arylacetic acids has been described by using a combination of CuSO4 as the catalyst and 2,2'-bipyridyl as the ligand in the presence of O-2 as an oxidant. The prominent features of this method are the use of readily available starting materials, inexpensive catalyst, broad substrate scope and high product yields.
引用
收藏
页码:1579 / 1583
页数:5
相关论文
共 29 条
[1]  
Alleca Sergio, 2003, Farmaco, V58, P639
[2]   Direct and catalytic synthesis of quinoxaline derivatives from epoxides and ene-1,2-diamines [J].
Antoniotti, S ;
Duñach, E .
TETRAHEDRON LETTERS, 2002, 43 (22) :3971-3973
[3]   Novel Quinoxaline-Based Organic Sensitizers for Dye-Sensitized Solar Cells [J].
Chang, Dong Wook ;
Lee, Hyo Joong ;
Kim, Jong H. ;
Park, Soo Young ;
Park, Su-Moon ;
Dai, Liming ;
Baek, Jong-Beom .
ORGANIC LETTERS, 2011, 13 (15) :3880-3883
[4]  
CHEESEMAN GW, 1965, CHEM IND-LONDON, P1382
[5]   Mesoporous carbon with controllable pore sizes as a support of the AuCl3 catalyst for acetylene hydrochlorination [J].
Chen, Kun ;
Kang, Lihua ;
Zhu, Mingyuan ;
Dai, Bin .
CATALYSIS SCIENCE & TECHNOLOGY, 2015, 5 (02) :1035-1040
[6]   Laterally-extended porphyrin systems incorporating a switchable unit [J].
Crossley, MJ ;
Johnston, LA .
CHEMICAL COMMUNICATIONS, 2002, (10) :1122-1123
[7]  
Dailey S, 2001, J MATER CHEM, V11, P2238, DOI 10.1039/b104674h
[8]  
Desplat V, 2008, J ENZYM INHIB MED CH, V23, P648, DOI [10.1080/14756360802205448, 10.1080/14756360802205448 ]
[9]   Synthesis and evaluation of the antiproliferative activity of novel pyrrolo[1,2-a]quinoxaline derivatives, potential inhibitors of Akt kinase. Part II [J].
Desplat, Vanessa ;
Moreau, Stephane ;
Gay, Aurore ;
Fabre, Solene Belisle ;
Thiolat, Denis ;
Massip, Stephane ;
Macky, Gregory ;
Godde, Frederic ;
Mossalayi, Djavad ;
Jarry, Christian ;
Guillon, Jean .
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2010, 25 (02) :204-215
[10]   Pyrroloquinoxaline hydrazones as fluorescent probes for amyloid fibrils [J].
Gemma, Sandra ;
Colombo, Laura ;
Forloni, Gianluigi ;
Savini, Luisa ;
Fracasso, Claudia ;
Caccia, Silvio ;
Salmona, Mario ;
Brindisi, Margherita ;
Joshi, Bhupendra P. ;
Tripaldi, Pierangela ;
Giorgi, Gianluca ;
Taglialatela-Scafati, Orazio ;
Novellino, Ettore ;
Fiorini, Isabella ;
Campiani, Giuseppe ;
Butini, Stefania .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (14) :5137-5148