Ytterbium triflate catalyzed heterocyclization of 1,2-phenylenediamines and alkyl oxalates under solvent-free conditions via Phillips reaction: A facile synthesis of quinoxaline-2,3-diones derivatives

被引：49

作者：

Wang, LM

Liu, JJ

Tian, H

Qian, CT

机构：

[1] E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Lab Organomet Chem, Shanghai, Peoples R China

来源：

SYNTHETIC COMMUNICATIONS | 2004年 / 34卷 / 08期

关键词：

quinoxaline-2,3-diones; Yb(OTf)(3); solvent-free synthesis; Phillips reaction;

D O I：

10.1081/SCC-120030683

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ytterbium triflate are found to catalyze efficiently the Phillips-type heterocyclization reactions of 1,2-phenylenediamine and alkyl oxalate under solvent-free and mild conditions to afford to the corresponding quinoxaline-2,3-dione derivatives in high yields. The catalyst could be recovered almost quantitatively from the aqueous layer after the reaction was completed and it could be reused in subsequent reaction without decrease in activity.

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收藏

页码：1349 / 1357

页数：9

相关论文

共 28 条

[1] 7-chloro-4,5-dihydro-8-(1,2,4-triazol-4-yl)4-oxo-1,2,4-triazolo[1,5-a]quinoxaline-2-carboxylates as novel highly selective AMPA receptor antagonists [J].

Catarzi, D ;

Colotta, V ;

Varano, F ;

Cecchi, L ;

Filacchioni, G ;

Galli, A ;

Costagli, C ;

Carlà, V .

JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (21) :3824-3826

[2] QUINOXALINES AND RELATED COMPOUNDS .6. SUBSTITUTION OF 2,3-DIHYDROXYQUINOXALINE AND ITS 1,4-DIMETHYL DERIVATIVE [J].

CHEESEMAN, GW .

JOURNAL OF THE CHEMICAL SOCIETY, 1962, (APR) :1170-&

[3]

Chen RF, 2001, CHINESE J CHEM, V19, P1225

[4] 1,2,4-triazolol[4,3-a]quinoxalin-1-one:: A versatile tool for the synthesis of potent and selective adenosine receptor antagonists [J].

Colotta, V ;

Catarzi, D ;

Varano, F ;

Cecchi, L ;

Filacchioni, G ;

Martini, C ;

Trincavelli, L ;

Lucacchini, A .

JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (06) :1158-1164

[5] SYNTHESIS AND EXCITATORY AMINO-ACID PHARMACOLOGY OF SOME NOVEL QUINOXALINEDIONES [J].

EPPERSON, JR ;

HEWAWASAM, P ;

MEANWELL, NA ;

BOISSARD, CG ;

GRIBKOFF, VK ;

POSTMUNSON, D .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (12) :2801-2804

[6] Structure-activity relationships of 1,4-dihydro-(1H,4H)-quinoxaline-2,3-diones as N-methyl-D-aspartate (glycine site) receptor antagonists.: 1.: Heterocyclic substituted 5-alkyl derivatives [J].

Fray, MJ ;

Bull, DJ ;

Carr, CL ;

Gautier, ECL ;

Mowbray, CE ;

Stobie, A .

JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (12) :1951-1962

[7] Photosensitization of guanine-specific DNA damage by a cyano-substituted quinoxaline di-N-oxide [J].

Fuchs, T ;

Gates, KS ;

Hwang, JT ;

Greenberg, MM .

CHEMICAL RESEARCH IN TOXICOLOGY, 1999, 12 (12) :1190-1194

[8] Synthesis of 5,12-dioxocyclam nickel (II) complexes having quinoxaline substituents at the 6 and 13 positions as potential DNA bis-intercalating and cleaving agents [J].

Hegedus, LS ;

Greenberg, MM ;

Wendling, JJ ;

Bullock, JP .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (11) :4179-4188

[9] Syntheses and structure-activity relationships of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-quinoxaline derivatives with retinoic acid receptor α agonistic activity [J].

Kikuchi, K ;

Hibi, S ;

Yoshimura, H ;

Tokuhara, N ;

Tai, K ;

Hida, T ;

Yamauchi, T ;

Nagai, M .

JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (03) :409-419

[10] Rare-earth metal triflates in organic synthesis [J].

Kobayashi, S ;

Sugiura, M ;

Kitagawa, H ;

Lam, WWL .

CHEMICAL REVIEWS, 2002, 102 (06) :2227-2302