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

页码：1546 / 1552

页数：7

共 76 条

[1] Roles of water for chemical reactions in high-temperature water [J].

Akiya, N ;

Savage, PE .

CHEMICAL REVIEWS, 2002, 102 (08) :2725-2750

[2] NEW METHOD OF PYRAZINE SYNTHESIS FOR FLAVOR USE [J].

AKIYAMA, T ;

ENOMOTO, Y ;

SHIBAMOTO, T .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1978, 26 (05) :1176-1179

[3] Synthesis and antimicrobial activities of some novel quinoxalinone derivatives [J].

Ali, MM ;

Ismail, MMF ;

El-Gaby, MSA ;

Zahran, MA ;

Ammar, YA .

MOLECULES, 2000, 5 (06) :864-873

[4]

[Anonymous], 2004, CHEM HETEROCYCLIC S2

[5] 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

[6] Facile synthesis of hydantoins and thiohydantoins in aqueous solution [J].

Baccolini, Graziano ;

Boga, Carla ;

Delpivo, Camilla ;

Micheletti, Gabriele .

TETRAHEDRON LETTERS, 2011, 52 (14) :1713-1717

[7]

BARLUENGA J, 1985, SYNTHESIS-STUTTGART, P313

[8] An efficient protocol for the synthesis of quinoxaline derivatives at room temperature using molecular iodine as the catalyst [J].

Bhosale, RS ;

Sarda, SR ;

Ardhapure, SS ;

Jadhav, WN ;

Bhusare, SR ;

Pawar, RP .

TETRAHEDRON LETTERS, 2005, 46 (42) :7183-7186

[9] ORTHO-NITROANILINE DERIVATIVES .8. SYNTHESIS OF SOME UNSYMMETRICAL DIMETHYLQUINOXALINES - A LONG-STANDING PROBLEM RESOLVED [J].

BLAIKLEY, DCW ;

CURRIE, DW ;

SMITH, DM ;

WATSON, SA ;

MCNAB, H .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (03) :367-369

[10] HYDROPHOBIC EFFECTS ON SIMPLE ORGANIC-REACTIONS IN WATER [J].

BRESLOW, R .

ACCOUNTS OF CHEMICAL RESEARCH, 1991, 24 (06) :159-164

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