A facile, metal- and solvent-free, autoxidative coupling of quinolines with indoles and pyrroles

被引:36
作者
Brasse, Mikael [2 ]
Ellman, Jonathan A. [1 ]
Bergman, Robert G. [2 ,3 ]
机构
[1] Yale Univ, Dept Chem, New Haven, CT 06520 USA
[2] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
[3] Univ Calif Berkeley, Lawrence Berkeley Lab, Div Chem Sci, Berkeley, CA 94720 USA
关键词
C-H FUNCTIONALIZATION; LEISHMANIA-DONOVANI; BOND FORMATION; N-OXIDES; HETEROCYCLES; DERIVATIVES;
D O I
10.1039/c1cc10507h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A simple, solvent-free, one-pot autoxidative coupling reaction between quinoline and indoles or pyrroles is reported. This atom economic method requires only a stoichiometric amount of inexpensive hydrochloric acid and does not require a catalyst.
引用
收藏
页码:5019 / 5021
页数:3
相关论文
共 43 条
[1]   Palladium-Catalyzed Dehydrogenative Direct Arylations of 1,2,3-Triazoles [J].
Ackermann, Lutz ;
Jeyachandran, Rajkumar ;
Potukuchi, Harish K. ;
Novak, Petr ;
Buettner, Lea .
ORGANIC LETTERS, 2010, 12 (09) :2056-2059
[2]   Intermolecular oxidative cross-coupling of arenes [J].
Ashenhurst, James A. .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (02) :540-548
[3]   Indolylquinoline derivatives are cytotoxic to Leishmania donovani promastigotes and amastigotes in vitro and are effective in treating murine visceral leishmaniasis [J].
Chakrabarti, G ;
Basu, A ;
Manna, PP ;
Mahato, SB ;
Mandal, NB ;
Bandyopadhyay, S .
JOURNAL OF ANTIMICROBIAL CHEMOTHERAPY, 1999, 43 (03) :359-366
[4]   Palladium-catalyzed C-H functionalization of pyridine N-oxides:: Highly selective alkenylation and direct arylation with unactivated arenes [J].
Cho, Seung Hwan ;
Hwang, Seung Jun ;
Chang, Sukbok .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (29) :9254-+
[5]  
d'Ischia M., 2008, Compr. Heterocycl. Chem. III, V3, P353
[6]   C-C bond formation via double C-H functionalization: Aerobic oxidative coupling as a method for synthesizing heterocoupled biaryls [J].
Dwight, Timothy A. ;
Rue, Nicholas R. ;
Charyk, Dagmara ;
Josselyn, Ryan ;
DeBoef, Brenton .
ORGANIC LETTERS, 2007, 9 (16) :3137-3139
[7]   Facile, solvent and ligand free iron catalyzed direct functionalization of N-protected tetrahydroisoquinolines and isochroman [J].
Ghobrial, Michael ;
Harhammer, Karin ;
Mihovilovic, Marko D. ;
Schnuerch, Michael .
CHEMICAL COMMUNICATIONS, 2010, 46 (46) :8836-8838
[8]   ELECTROPHILIC AROMATIC-SUBSTITUTION REACTIONS WITH PROTONATED 1,3-DIAZINES .1. PREPARATION AND PROPERTIES OF 4-ARYL-SUBSTITUTED 3,4-DIHYDROPYRIMIDINE DERIVATIVES [J].
GIRKE, WPK .
CHEMISCHE BERICHTE-RECUEIL, 1979, 112 (01) :1-15
[9]  
HAMANA M, 1967, CHEM PHARM BULL, V15, P363
[10]  
Hauske JR, 2002, [No title captured], Patent No. [US637667081, 6376670, US6376670]