One-pot synthesis of 1,2-disubstituted pyrrolo[2,3-b]quinoxalines via palladium-catalyzed heteroannulation in water

被引:38
作者
Keivanloo, Ali [1 ]
Bakherad, Mohammad [1 ]
Rahimi, Amin [1 ]
Taheri, Sayed Ali Naghi [1 ]
机构
[1] Shahrood Univ Technol, Sch Chem, Shahrood, Iran
关键词
Palladium; Pyrroloquinoxaline; Alkyne; Sonogashira reaction; SONOGASHIRA COUPLING REACTION; 5-HT3 RECEPTOR AGONISTS; ARYL CHLORIDES; AQUEOUS-MEDIA; DERIVATIVES; HETEROCYCLIZATION; CHEMISTRY; ANALOGS; ALKYNES; DESIGN;
D O I
10.1016/j.tetlet.2010.02.123
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of N-alkyl-3-chloroquinoxaline-2-amines with 1-alkynes, catalyzed by Pd-Cu, in the presence of sodium lauryl sulfate as the surfactant in water, leads to the one-pot formation of 1,2-disubstituted pyrrolo[2,3-b]quinoxalines in good-to-high yields. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2409 / 2412
页数:4
相关论文
共 52 条
[1]  
AMES DE, 1985, J CHEM RES, P144
[2]   General catalysts for the Suzuki-Miyaura and Sonogashira coupling reactions of aryl chlorides and for the coupling of challenging substrate combinations in water [J].
Anderson, KW ;
Buchwald, SL .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (38) :6173-6177
[3]   Synthesis of 2-benzylimidazo[2,1-b][1,3]benzothiazoles through palladium-catalyzed heteroannulation of acetylenic compounds [J].
Bakherad, Mohammad ;
Nasr-Isfahani, Hossein ;
Keivanloo, Ali ;
Sang, Golnaz .
TETRAHEDRON LETTERS, 2008, 49 (43) :6188-6191
[4]   Pd-Cu catalyzed heterocyclization during Sonogashira coupling:: synthesis of 2-benzylimidazo[1,2-a]pyridine [J].
Bakherad, Mohammad ;
Nasr-Isfahani, Hossein ;
Keivanloo, Ali ;
Doostmohammadi, Nesa .
TETRAHEDRON LETTERS, 2008, 49 (23) :3819-3822
[5]   Palladium catalyzed alkynylation of aryl halides (Sonogashira reaction) in water [J].
Bhattacharya, S ;
Sengupta, S .
TETRAHEDRON LETTERS, 2004, 45 (47) :8733-8736
[6]   Self-assembly of folded m-phenylene ethynylene oligomers into helical columns [J].
Brunsveld, L ;
Meijer, EW ;
Prince, RB ;
Moore, JS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (33) :7978-7984
[7]   Catalytic coupling of terminal acetylenes with iodoarenes and diaryliodonium salts in water [J].
Bumagin, NA ;
Sukhomlinova, LI ;
Luzikova, EV ;
Tolstaya, TP ;
Beletskaya, IP .
TETRAHEDRON LETTERS, 1996, 37 (06) :897-900
[8]   Synthesis and anti-inflammatory/antioxidant activities of some new ring substituted 3-phenyl-1-(1,4-di-N-oxide quinoxalin-2-yl)-2-propen-1-one derivatives and of their 4,5-dihydro-(1H)-pyrazole analogues [J].
Burguete, Asuncion ;
Pontiki, Eleni ;
Hadjipavlou-Litina, Dimitra ;
Villar, Raquel ;
Vicente, Esther ;
Solano, Beatriz ;
Ancizu, Saioa ;
Perez-Silanes, Silvia ;
Aldana, Ignacio ;
Monge, Antonio .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (23) :6439-6443
[9]   Pyrroloquinoxaline derivatives as high-affinity and selective 5-HT3 receptor agonists:: Synthesis, further structure-activity relationships, and biological studies [J].
Campiani, G ;
Morelli, E ;
Gemma, S ;
Nacci, V ;
Butini, S ;
Hamon, M ;
Novellino, E ;
Greco, G ;
Cagnotto, A ;
Goegan, M ;
Cervo, L ;
Dalla Valle, F ;
Fracasso, C ;
Caccia, S ;
Mennini, T .
JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (21) :4362-4379
[10]   Novel and highly potent 5-HT3 receptor agonists based on a pyrroloquinoxaline structure [J].
Campiani, G ;
Cappelli, A ;
Nacci, V ;
Anzini, M ;
Vomero, S ;
Hamon, M ;
Cagnotto, A ;
Fracasso, C ;
Uboldi, C ;
Caccia, S ;
Consolo, S ;
Mennini, T .
JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (22) :3670-3678