A Green Synthesis of Quinoxalines and 2,3-Dihydropyrazines

被引:25
作者
Delpivo, Camilla [1 ]
Micheletti, Gabriele [1 ]
Boga, Carla [1 ]
机构
[1] Dept Ind Chem Toso Montanari, I-40136 Bologna, Italy
来源
SYNTHESIS-STUTTGART | 2013年 / 45卷 / 11期
关键词
quinoxaline; dihydropyrazine; green; water; condensation; DNA STRAND-BREAKAGE; TYROSINE KINASE-ACTIVITY; ALPHA-HYDROXY KETONES; ONE-POT SYNTHESIS; RECEPTOR ANTAGONISTS; EFFICIENT SYNTHESIS; CATALYZED SYNTHESIS; ORGANIC-REACTIONS; TANDEM OXIDATION; DERIVATIVES;
D O I
10.1055/s-0033-1338441
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Quinoxaline and dihydropyrazine derivatives were obtained in high yields by simple addition of 1,2-diamines and 1,2-dicarbonyl compounds in water. In some cases, the products spontaneously precipitated from the reaction mixture, making it possible to recover and reuse the mother liquor for further condensations. The very mild reaction conditions, the high yields of the products, and the absence of any catalyst make this methodology an efficient and green route to quinoxalines and dihydropyrazines.
引用
收藏
页码:1546 / 1552
页数:7
相关论文
共 76 条
[51]   Gallium (III) triflate-catalyzed synthesis of heterocycles: quinoxalines, 1,5-benzodiazepines and their fluorinated derivatives [J].
Prakash, G. K. Surya ;
Vaghoo, Habiba ;
Venkat, Arthi ;
Panja, Chiradeep ;
Chacko, Sujith ;
Mathew, Thomas ;
Olah, George A. .
FUTURE MEDICINAL CHEMISTRY, 2009, 1 (05) :909-920
[52]  
Pranab Ghosh., 2011, Advances in Applied Science Research, V2, P255
[53]   DABCO-Catalyzed Oxidation of Deoxybenzoins to Benzils with Air and One-Pot Synthesis of Quinoxalines [J].
Qi, Chaorong ;
Jiang, Huanfeng ;
Huang, Liangbin ;
Chen, Zhengwang ;
Chen, Huoji .
SYNTHESIS-STUTTGART, 2011, (03) :387-396
[54]   Preparation of quinoxalines, dihydropyrazines, pyrazines and piperazines using tandem oxidation processes [J].
Raw, SA ;
Wilfred, CD ;
Taylor, RJK .
CHEMICAL COMMUNICATIONS, 2003, (18) :2286-2287
[55]   HYDROPHOBIC ACCELERATION OF DIELS-ALDER REACTIONS [J].
RIDEOUT, DC ;
BRESLOW, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (26) :7816-7817
[56]   Quinoxaline synthesis from α-hydroxy ketones via a tandem oxidation process using catalysed aerobic oxidation [J].
Robinson, RS ;
Taylor, RJK .
SYNLETT, 2005, (06) :1003-1005
[57]   Phototransformations of 6-X-5-nitroquinoxalines [J].
Rtishchev, NI ;
Selitrennikov, AV .
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2004, 74 (03) :428-437
[58]   Synthetic water-oxidation catalysts for artificial photosynthetic water oxidation [J].
Ruttinger, W ;
Dismukes, GC .
CHEMICAL REVIEWS, 1997, 97 (01) :1-24
[59]  
SAKATA G, 1988, HETEROCYCLES, V27, P2481
[60]   4-AMINO[1,2,4]TRIAZOLO[4,3-A]QUINOXALINES - A NOVEL CLASS OF POTENT ADENOSINE RECEPTOR ANTAGONISTS AND POTENTIAL RAPID-ONSET ANTIDEPRESSANTS [J].
SARGES, R ;
HOWARD, HR ;
BROWNE, RG ;
LEBEL, LA ;
SEYMOUR, PA ;
KOE, BK .
JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (08) :2240-2254