Reaction of quinoxalin-2-ones with TosMIC reagent:: synthesis of imidazo[1,5-a]quinoxalin-4-ones

被引：42

作者：

Chen, P ^{[1
]}

Barrish, JC ^{[1
]}

Iwanowicz, E ^{[1
]}

Lin, J ^{[1
]}

Bednarz, MS ^{[1
]}

Chen, BC ^{[1
]}

机构：

[1] Bristol Myers Squibb Co, Pharmaceut Res Inst, Discovery Chem, Princeton, NJ 08543 USA

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 26期

关键词：

D O I：

10.1016/S0040-4039(01)00697-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Imidazo[1,5-alpha ]quinoxalin-4-ones were prepared in four steps starting from 1,2-phenylenediamines using a new strategy for the construction of the ring system. A key step in this new method involves the reaction of quinoxalin-2-ones with TosMIC (tosylmethyl isocyanide). (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：4293 / 4295

页数：3

共 16 条

[1]

[Anonymous], 1989, EP P., Patent No. 344943

[2]

Barrish J.C., 1999, [No title captured], Patent No. [WO 99/09845, 9909845]

[3] 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

[4] A new facile method for the synthesis of 1-arylimidazole-5-carboxylates [J].

Chen, BC ;

Bednarz, MS ;

Zhao, RL ;

Sundeen, JE ;

Chen, P ;

Shen, ZQ ;

Skoumbourdis, AP ;

Barrish, JC .

TETRAHEDRON LETTERS, 2000, 41 (29) :5453-5456

[5] ORTHO-NITROANILINE DERIVATIVES .13. REACTIONS OF N-(ORTHO-NITROARYL)SARCOSINE ESTERS WITH BASES [J].

COLLINS, PA ;

MCFARLANE, MD ;

MACKIE, RK ;

SMITH, DM .

TETRAHEDRON, 1992, 48 (37) :7887-7898

[6]

COLLTTA V, 1995, EUR J MED CHEM, V30, P133

[7] Total syntheses of taliscanine, velutinam, and enterocarpam II [J].

Couture, A ;

Deniau, E ;

Grandclaudon, P ;

Hoarau, C .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (09) :3128-3132

[8] NOVEL COMPOUNDS POSSESSING POTENT CAMP AND CGMP PHOSPHODIESTERASE INHIBITORY ACTIVITY - SYNTHESIS AND CARDIOVASCULAR EFFECTS OF A SERIES OF IMIDAZO[1,2-A]QUINOXALINONES AND IMIDAZO[1,5-A]QUINOXALINONES AND THEIR AZA ANALOGS [J].

DAVEY, DD ;

ERHARDT, PW ;

CANTOR, EH ;

GREENBERG, SS ;

INGEBRETSEN, WR ;

WIGGINS, J .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (09) :2671-2677

[9] 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

[10] SYNTHESES OF 2-MONOSUBSTITUTED AND 2-3-DISUBSTITUTED QUINOXALINES [J].

GOWENLOCK, AH ;

NEWBOLD, GT ;

SPRING, FS .

JOURNAL OF THE CHEMICAL SOCIETY, 1945, :622-625

← 1 2 →